Product Name

  • Name

    Ethyl isobutyrylacetate

  • EINECS 230-491-9
  • CAS No. 7152-15-0
  • Article Data52
  • CAS DataBase
  • Density 0.979 g/cm3
  • Solubility
  • Melting Point -9 °C(lit.)
  • Formula C8H14O3
  • Boiling Point 173 °C at 760 mmHg
  • Molecular Weight 158.197
  • Flash Point 53.3 °C
  • Transport Information UN 3272 3/PG 3
  • Appearance clear colorless to yellow liquid
  • Safety 16
  • Risk Codes 10
  • Molecular Structure Molecular Structure of 7152-15-0 (Ethyl isobutyrylacetate)
  • Hazard Symbols R10:;
  • Synonyms Valericacid, 4-methyl-3-oxo-, ethyl ester (6CI,8CI);4-Methyl-3-oxo-pentanoic acidethyl ester;4-Methyl-3-oxovaleric acid ethyl ester;Ethyl4-methyl-3-oxopentanoate;Ethyl 4-methyl-3-oxovalerate;Isobutyrylacetic acid ethyl ester;NSC 62029;g,g-Dimethylacetoacetic acid ethyl ester;
  • PSA 43.37000
  • LogP 1.16470

Synthetic route

isobutyryl chloride
79-30-1

isobutyryl chloride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
Stage #1: ethyl potassium malonate With triethylamine; magnesium chloride In ethyl acetate at 0 - 35℃; for 6.5h;
Stage #2: isobutyryl chloride In ethyl acetate at 0 - 20℃; for 13h; Time;		61%
With triethylamine; magnesium chloride In acetonitrile
diethyl isobutyrylmalonate
21633-78-3

diethyl isobutyrylmalonate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water for 8h; Reflux;54%
With isobutyric Acid; copper diacetate; magnesium oxide Heating;
With copper diacetate; magnesium oxide; isobutyric Acid at 145℃; for 14h;
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With sodium hydride In toluene; mineral oil Reflux;60%
With sodium hydride at 60 - 90℃;
With sodium hydride In benzene
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

N,N,N,N,N,N-hexamethylphosphoric triamide
680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
In methanol; paraffin oil; benzene81%
...Expand
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

isobutyryl chloride
79-30-1

isobutyryl chloride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran99%
Stage #1: hydrogen ethyl malonate With [2,2]bipyridinyl; n-butyllithium In tetrahydrofuran; hexane at -70 - -10℃; Inert atmosphere;
Stage #2: isobutyryl chloride In tetrahydrofuran; hexane at -65℃; for 0.166667h; Inert atmosphere;		80%
2-isobutyryl-acetoacetic acid ester

2-isobutyryl-acetoacetic acid ester

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With sodium hydroxide
With diethyl ether; ammonia at 25℃;
With ammonium hydroxide at 40℃;
Ethyl (+/-)-3-hydroxy-4-methyl-4-pentenoate
122622-90-6

Ethyl (+/-)-3-hydroxy-4-methyl-4-pentenoate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In water; acetone at 60℃; for 16h; chemoselective reaction;91%
ethyl 2-diazo-3-hydroxy-4-methylpentanoate
38491-54-2

ethyl 2-diazo-3-hydroxy-4-methylpentanoate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In neat (no solvent) at 20℃; for 9h;60%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

N-(methylpropionyl)oxazolidin-2-one
109853-52-3

N-(methylpropionyl)oxazolidin-2-one

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With zinc In tetrahydrofuran 1) 30 deg C, 2 h, 2) reflux, 18 h;83%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

ethanol
64-17-5

ethanol

isobutyric Acid
79-31-2

isobutyric Acid

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; isobutyric Acid With dmap In dichloromethane at 20℃; for 0.25h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃;
Stage #3: ethanol In toluene for 3h; Reflux;		48%
...Expand
ethyl bromoacetate
105-36-2

ethyl bromoacetate

1-(2'-Methyl)propanoyl-3,5-dimethylpyrazole
155688-65-6

1-(2'-Methyl)propanoyl-3,5-dimethylpyrazole

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With zinc In tetrahydrofuran for 1h; Heating;73%
ethyl acetate
141-78-6

ethyl acetate

isobutyryl chloride
79-30-1

isobutyryl chloride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; Condensation;
4-methyl-3-oxopentanonitrile
29509-06-6

4-methyl-3-oxopentanonitrile

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With hydrogenchloride; ethanol
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With cetyltrimethylammonium chloride; calcium carbonate; calcium oxide In 1,4-dioxane at 25℃; for 5h; Sonication;95 %Chromat.
ethyl potassium malonate
6148-64-7

ethyl potassium malonate

isobutyric Acid
79-31-2

isobutyric Acid

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
Stage #1: isobutyric Acid With 1,1'-carbonyldiimidazole In tetrahydrofuran Acylation;
Stage #2: ethyl potassium malonate With magnesium chloride In tetrahydrofuran Substitution; decarboxylation;
With 1,1'-carbonyldiimidazole; magnesium chloride In tetrahydrofuran
ethanol
64-17-5

ethanol

5-(1-hydroxy-2-methylpropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
84794-38-7

5-(1-hydroxy-2-methylpropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
In toluene for 3h; Reflux;43%
In toluene Heating;
In toluene for 3h; Reflux;2.24 g
ethyl bromoacetate
105-36-2

ethyl bromoacetate

isobutyryl chloride
79-30-1

isobutyryl chloride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With zinc; tetrakis(triphenylphosphine) palladium(0) 1.) DME; 2.) DME, reflux, 1 h; Yield given. Multistep reaction;
isobutyrylacetoacetic acid ester

isobutyrylacetoacetic acid ester

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With sodium hydroxide
With sodium ethanolate
2-Benzenesulfinyl-3-hydroxy-4-methyl-pentanoic acid ethyl ester
57365-40-9

2-Benzenesulfinyl-3-hydroxy-4-methyl-pentanoic acid ethyl ester

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
In benzene
ethanol
64-17-5

ethanol

5-(1-Amino-2-methyl-propylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
77570-22-0

5-(1-Amino-2-methyl-propylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With hydrogenchloride; sodium ethanolate 1.) ethanol, reflux, overnight; Yield given. Multistep reaction;
ethyl 2-acetyl-4-methyl-3-oxopentanoate
79322-87-5

ethyl 2-acetyl-4-methyl-3-oxopentanoate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With ethanol; sodium ethanolate
4-methyl-2-pentynoic acid
65199-69-1

4-methyl-2-pentynoic acid

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alcoholic KOH-solution
2: sulfuric acid
View Scheme
ethanol
64-17-5

ethanol

isobutyrylacetic acid
5650-76-0

isobutyrylacetic acid

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With sulfuric acid
ethyl bromoacetate
105-36-2

ethyl bromoacetate

Ethyl isobutyrate
97-62-1

Ethyl isobutyrate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With iodine; magnesium
diethyl isobutyrylmalonate
21633-78-3

diethyl isobutyrylmalonate

isobutyric Acid
79-31-2

isobutyric Acid

A

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

B

ethyl isobutyrate, 2,6-dimethyl-heptane-3,5-dione

ethyl isobutyrate, 2,6-dimethyl-heptane-3,5-dione

Conditions
ConditionsYield
With copper diacetate; magnesium oxide
...Expand
(4-methyl-3-oxo-1-phenyl-pentyl)-malonic acid diethyl ester
5435-09-6

(4-methyl-3-oxo-1-phenyl-pentyl)-malonic acid diethyl ester

sodium ethanolate
141-52-6

sodium ethanolate

A

diethyl benzalmalonate
5292-53-5

diethyl benzalmalonate

B

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

C

Ethyl isobutyrate
97-62-1

Ethyl isobutyrate

D

diphenyl-diisobutyryl-cyclobutane

diphenyl-diisobutyryl-cyclobutane

Conditions
ConditionsYield
at 130℃;
...Expand
ethyl acetate
141-78-6

ethyl acetate

C7H12O4
62763-38-6

C7H12O4

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
(i) LDA, Et2O, THF, (ii) /BRN= 6775142/; Multistep reaction;
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

sodium methylate
124-41-4

sodium methylate

Diethyl carbonate
105-58-8

Diethyl carbonate

A

Methyl 4-methyl-3-oxopentanoate
42558-54-3

Methyl 4-methyl-3-oxopentanoate

B

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

...Expand
tetrachloromethane
56-23-5

tetrachloromethane

ethyl 2-acetyl-4-methyl-3-oxopentanoate
79322-87-5

ethyl 2-acetyl-4-methyl-3-oxopentanoate

water
7732-18-5

water

A

acetic acid
64-19-7

acetic acid

B

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
Erhitzen;
...Expand
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

2-bromo-4-methyl-3-oxo-pentanoic acid ethyl ester
81569-67-7

2-bromo-4-methyl-3-oxo-pentanoic acid ethyl ester

Conditions
ConditionsYield
With N-Bromosuccinimide In various solvent(s) at 20℃; for 0.916667h;92%
With bromine In tetrachloromethane; water at 0℃; for 2h;90%
With bromine In tetrachloromethane; water at 0℃; for 2h;90%
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

Ethyl 3-amino-4-methyl-2-pentenoate
70106-45-5

Ethyl 3-amino-4-methyl-2-pentenoate

Conditions
ConditionsYield
With ammonium acetate; acetic acid In water; toluene Reflux;88.6%
With ammonium acetate In methanol at 20℃; for 72h;85%
With ammonium acetate In methanol at 20℃; for 72h; Substitution;
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

methyl iodide
74-88-4

methyl iodide

ethyl 2,4-dimethyl-3-oxopentanoate
7251-96-9

ethyl 2,4-dimethyl-3-oxopentanoate

Conditions
ConditionsYield
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With potassium carbonate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃;		89%
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With potassium carbonate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 0℃; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h; Inert atmosphere;
With potassium carbonate In tetrahydrofuran Inert atmosphere; Reflux;
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 2-chloro-4-methyl-3-oxopentanoate
35391-60-7

ethyl 2-chloro-4-methyl-3-oxopentanoate

Conditions
ConditionsYield
With N-chloro-succinimide In various solvent(s) at 20℃; for 1h;92%
With sulfuryl dichloride In toluene at 20℃; for 18h;70%
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With sulfuryl dichloride In toluene at 20℃; for 18h;
Stage #2: With water In toluene		70%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester
122930-45-4

(E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester

Conditions
ConditionsYield
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 22h;95%
With piperidine; acetic acid In benzene Heating;86.7%
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 22h; Inert atmosphere;83.9%
With piperidine; acetic acid In toluene for 8h; Heating;75%
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 22h; Inert atmosphere;
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 3-amino-4-methyl-pent-2-enoate
78168-82-8

ethyl 3-amino-4-methyl-pent-2-enoate

Conditions
ConditionsYield
With ammonium acetate In cyclohexane; isopropyl alcohol98%
With ammonium acetate In methanol at 20℃; for 72h;85%
With ammonia In ethanol at 25℃; for 42h;
With ammonium acetate In cyclohexane
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl (3R)-3-hydroxy-4-methylpentanoate
95614-86-1

ethyl (3R)-3-hydroxy-4-methylpentanoate

Conditions
ConditionsYield
With hydrogen; (S)-BinapRuBr2 at 50℃; under 760 Torr; for 48h;100%
With C32H40F6O6P2Pd; hydrogen In acetone at 0℃; under 23272.3 Torr; for 12h; Autoclave; enantioselective reaction;99%
With (2R,2'R,3R,3'R)-3,3'-di-tert-butyl-2,2'-diisopropyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole; hydrogen; palladium diacetate In acetone at 0 - 20℃; under 225023 Torr; for 20h; Glovebox;99%
6-bromo-1H-indole-2-carbaldehyde
105191-12-6

6-bromo-1H-indole-2-carbaldehyde

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(2Z)-2-((6-bromo-1H-indol-2-yl)methylidene)-4-methyl-3-oxopentanoic acid ethyl ester

(2Z)-2-((6-bromo-1H-indol-2-yl)methylidene)-4-methyl-3-oxopentanoic acid ethyl ester

Conditions
ConditionsYield
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 12h; Aldol Condensation; Inert atmosphere;95%
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 12h; Inert atmosphere;95%
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 12h; Inert atmosphere;95%
8-bromo-quinoline-4-carbaldehyde
898391-87-2

8-bromo-quinoline-4-carbaldehyde

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl (Z)-2-((8-bromo-quinolin-4-yl)methylene)-4-methyl-3-oxopentanoate

ethyl (Z)-2-((8-bromo-quinolin-4-yl)methylene)-4-methyl-3-oxopentanoate

Conditions
ConditionsYield
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 12h; Inert atmosphere;89%
With pyridine; acetic acid In isopropyl alcohol at 20℃; for 12h; Inert atmosphere;89%
With piperidine; acetic acid In isopropyl alcohol at 20℃; for 12h; Inert atmosphere;89%
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

isobutyrylacetic acid
5650-76-0

isobutyrylacetic acid

Conditions
ConditionsYield
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With sodium hydroxide; water at 20℃; for 16h;
Stage #2: With hydrogenchloride In water pH=1 - 2;		95%
With water; sodium hydroxide at 0 - 20℃; for 16h;
3-(4-fluoro-phenyl)-propenal
51791-26-5, 24654-55-5

3-(4-fluoro-phenyl)-propenal

thiourea
17356-08-0

thiourea

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 4-(4-fluorostyryl)-6-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 4-(4-fluorostyryl)-6-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: 3-(4-fluoro-phenyl)-propenal; thiourea With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		92%
Stage #1: 3-(4-fluoro-phenyl)-propenal; thiourea With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; enantioselective reaction;		92%
Stage #1: 3-(4-fluoro-phenyl)-propenal; thiourea With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		92%
...Expand
4-chlorocinnamaldehyde
1075-77-0

4-chlorocinnamaldehyde

thiourea
17356-08-0

thiourea

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 4-(4-chlorostyryl)-6-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 4-(4-chlorostyryl)-6-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: 4-chlorocinnamaldehyde; thiourea With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		93%
Stage #1: 4-chlorocinnamaldehyde; thiourea With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; enantioselective reaction;		93%
Stage #1: 4-chlorocinnamaldehyde; thiourea With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		93%
...Expand
4-bromocinnamaldeyde
49678-04-8, 3893-18-3

4-bromocinnamaldeyde

thiourea
17356-08-0

thiourea

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 4-(4-bromostyryl)-6-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 4-(4-bromostyryl)-6-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: 4-bromocinnamaldeyde; thiourea With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		93%
Stage #1: 4-bromocinnamaldeyde; thiourea With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; enantioselective reaction;		93%
Stage #1: 4-bromocinnamaldeyde; thiourea With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		93%
...Expand
4-(trifluoromethyl)cinnamaldehyde
95123-61-8, 41917-83-3

4-(trifluoromethyl)cinnamaldehyde

thiourea
17356-08-0

thiourea

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 6-isopropyl-2-thioxo-4-(4-(trifluoromethyl)styryl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 6-isopropyl-2-thioxo-4-(4-(trifluoromethyl)styryl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: 4-(trifluoromethyl)cinnamaldehyde; thiourea With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		90%
Stage #1: 4-(trifluoromethyl)cinnamaldehyde; thiourea With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; enantioselective reaction;		90%
Stage #1: 4-(trifluoromethyl)cinnamaldehyde; thiourea With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		90%
...Expand
3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

thiourea
17356-08-0

thiourea

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 6-isopropyl-4-(4-nitrostyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 6-isopropyl-4-(4-nitrostyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: 3-(4-nitrophenyl)-2-propenal; thiourea With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		91%
Stage #1: 3-(4-nitrophenyl)-2-propenal; thiourea With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; enantioselective reaction;		91%
Stage #1: 3-(4-nitrophenyl)-2-propenal; thiourea With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		91%
...Expand
thiourea
17356-08-0

thiourea

3-(4-methylphenyl)acrylaldehyde
1504-75-2

3-(4-methylphenyl)acrylaldehyde

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 6-isopropyl-4-(4-methylstyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 6-isopropyl-4-(4-methylstyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: thiourea; 4-methyl cinnamaldehyde With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		96%
Stage #1: thiourea; 4-methyl cinnamaldehyde With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; enantioselective reaction;		96%
Stage #1: thiourea; 4-methyl cinnamaldehyde With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		96%
...Expand
4-methoxycinnamaldehyde
1963-36-6

4-methoxycinnamaldehyde

thiourea
17356-08-0

thiourea

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 6-isopropyl-4-(4-methoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 6-isopropyl-4-(4-methoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: 4-methoxycinnamaldehyde; thiourea With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		95%
Stage #1: 4-methoxycinnamaldehyde; thiourea With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; enantioselective reaction;		95%
Stage #1: 4-methoxycinnamaldehyde; thiourea With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		95%
...Expand
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 2-diazo-4-methyl-3-oxopentanoate
402568-02-9

ethyl 2-diazo-4-methyl-3-oxopentanoate

Conditions
ConditionsYield
With 4-toluenesulfonyl azide; caesium carbonate In tetrahydrofuran at 25℃; for 3h; Inert atmosphere;87%
With sodium azide; 3-Carboxybenzenesulfonyl chloride; potassium carbonate In water; acetonitrile at 20℃; for 2h;85%
With 4-toluenesulfonyl azide; triethylamine
3-(4-bromophenyl)-2-(trifluoromethyl)acrylic acid ethyl ester

3-(4-bromophenyl)-2-(trifluoromethyl)acrylic acid ethyl ester

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

3,5-diethyl 4-(4-bromophenyl)-2-fluoro-6-(propan-2-yl)-4H-pyran-3,5-dicarboxylate

3,5-diethyl 4-(4-bromophenyl)-2-fluoro-6-(propan-2-yl)-4H-pyran-3,5-dicarboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere;86%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; Molecular sieve;86%
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 3,3-difluoro-4-methylpentanoate

ethyl 3,3-difluoro-4-methylpentanoate

Conditions
ConditionsYield
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With sulfur tetrafluoride; hydrogen fluoride at 20℃; Cooling with liquid nitrogen; Autoclave;
Stage #2: With potassium permanganate In dichloromethane; water for 1h;		78%
guanidine hydrochloride
50-01-1

guanidine hydrochloride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

2-amino-6-isopropyl-4(3H)-pyrimidinone

2-amino-6-isopropyl-4(3H)-pyrimidinone

Conditions
ConditionsYield
With sodium methylate In methanol; ethanol at 100℃; Sealed tube;76%
With sodium methylate In ethanol for 2h; Heating;71.5%
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

benzylamine
100-46-9

benzylamine

ethyl 5-(propan-2-yl)-2-phenyl-1,3-oxazole-4-carboxylate
1354790-43-4

ethyl 5-(propan-2-yl)-2-phenyl-1,3-oxazole-4-carboxylate

Conditions
ConditionsYield
With tert-butyl hydroxyperoxide; tetra-(n-butyl)ammonium iodide In water; ethyl acetate at 40℃; for 10h;76%
With [Cu(1,10-phenanthroline)2Cl]Cl; iodine; oxygen In acetonitrile at 60℃; for 24h; Molecular sieve;75%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

urea
57-13-6

urea

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 4-(4-fluorophenyl)-6-isopropyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate

ethyl 4-(4-fluorophenyl)-6-isopropyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate

Conditions
ConditionsYield
With sulfuric acid In ethanol at 80℃; for 48h;99%
With cerium(III) chloride heptahydrate In ethanol at 80℃; for 24h; Biginelli Pyrimidone Synthesis;38%
...Expand
thiourea
17356-08-0

thiourea

3-phenyl-propenal
104-55-2

3-phenyl-propenal

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(S)-ethyl 6-isopropyl-4-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

(S)-ethyl 6-isopropyl-4-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Stage #1: thiourea; 3-phenyl-propenal With quinidine thiourea A; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Biginelli Pyrimidone Synthesis; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate In dichloromethane at 50℃; for 15h; Biginelli Pyrimidone Synthesis; Sealed tube; enantioselective reaction;		96%
Stage #1: thiourea; 3-phenyl-propenal With C30H29F6N3OS; (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid In dichloromethane at 20℃; for 3h; Sealed tube;
Stage #2: ethyl 4-methyl-3-oxo-pentanoate at 50℃; for 15h; enantioselective reaction;		96%
...Expand
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

(E)-3-amino-4-methyl-2-thiocyanatopent-2-enoic acid ethyl ester

(E)-3-amino-4-methyl-2-thiocyanatopent-2-enoic acid ethyl ester

Conditions
ConditionsYield
With fluorescein free acid In acetonitrile at 20℃; UV-irradiation;80%
With fluorescein In acetonitrile at 20℃; for 6h; Irradiation;80%
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 2-hydroxyimino-4-methyl-3-oxo-pentanoate
38603-76-8

ethyl 2-hydroxyimino-4-methyl-3-oxo-pentanoate

Conditions
ConditionsYield
With acetic acid; sodium nitrite In water at 0℃;100%
With sodium nitrite In acetic acid at 0 - 20℃;90%
With sodium nitrite In water; acetic acid at 0 - 20℃;90%
With sodium nitrite In water; acetic acid at 5 - 20℃; for 2h;
With acetic acid; sodium nitrite In water at 0 - 20℃;
benzamidine monohydrochloride
1670-14-0

benzamidine monohydrochloride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

6-isopropyl-2-phenylpyrimidin-4-ol

6-isopropyl-2-phenylpyrimidin-4-ol

Conditions
ConditionsYield
With potassium tert-butylate In methanol at 0℃; for 4.5h; Reflux;78.2%
With potassium carbonate In water at 20℃; for 0.25h; Microwave irradiation;54%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

diethyl 2,6-diisopropylpyridine-3,5-dicarboxylate

diethyl 2,6-diisopropylpyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With copper(I) oxide; tert.-butylhydroperoxide; ammonium acetate In water at 120℃; for 24h;68%
With copper(I) oxide; tert.-butylhydroperoxide; ammonium acetate at 120℃; for 24h; Schlenk technique;58%
[5-bromo-3-methylpent-2-en-1-yl]benzene
1001653-19-5

[5-bromo-3-methylpent-2-en-1-yl]benzene

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 5-methyl-2-(2-methylpropanoyl)-7-phenylhept-4-enoate

ethyl 5-methyl-2-(2-methylpropanoyl)-7-phenylhept-4-enoate

Conditions
ConditionsYield
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With sodium hydride In tetrahydrofuran; mineral oil for 1h; Cooling;
Stage #2: [5-bromo-3-methylpent-2-en-1-yl]benzene In tetrahydrofuran; mineral oil at 0 - 20℃; for 18h;		98%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

ethyl 4-methyl-3-{[(trifluoromethyl)sulfonyl]oxy}pent-2-enoate

ethyl 4-methyl-3-{[(trifluoromethyl)sulfonyl]oxy}pent-2-enoate

Conditions
ConditionsYield
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With lithium hydroxide In water; toluene at 5 - 10℃;
Stage #2: trifluoromethylsulfonic anhydride In water; toluene at 5 - 15℃;		67%
Stage #1: ethyl 4-methyl-3-oxo-pentanoate With water; lithium hydroxide In toluene at 10℃; for 0.0833333h;
Stage #2: trifluoromethylsulfonic anhydride In toluene at 10 - 25℃; for 2h;

Ethyl isobutyrylacetate Chemical Properties

IUPAC    Name: Ethyl 4-methyl-3-oxopentanoate      
Empirical Formula: C8H14O3
Molecular Weight: 158.195 
Einecs: 230-491-9 
Freely Rotating Bonds: 5
Polar Surface Area: 43.37 Å2
Index of Refraction: 1.419
Molar Refractivity: 40.87 cm3
Molar Volume: 161.5 cm3
Polarizability: 16.2 ×10-24 cm3
Surface Tension: 29.8 dyne/cm
Density: 0.979 g/cm3
Flash Point: 53.3 °C
Enthalpy of Vaporization: 40.94 kJ/mol
Boiling Point: 173 °C at 760 mmHg
Vapour Pressure: 1.29 mmHg at 25°C 
The Cas Register Number of  Pentanoic acid,4-methyl-3-oxo-, ethyl ester is 7152-15-0.The chemical synonyms of  Pentanoic acid,4-methyl-3-oxo-, ethyl ester (CAS NO.7152-15-0) are Ethyl isobutyrylacetate .The molecular structure of  Pentanoic acid,4-methyl-3-oxo-, ethyl ester (CAS NO.7152-15-0) is
.

Ethyl isobutyrylacetate Uses

  Pentanoic acid,4-methyl-3-oxo-, ethyl ester (CAS NO.7152-15-0) is used in organic synthesis.

Ethyl isobutyrylacetate Safety Profile

Risk Statements: 10
Safety Statements: 16
RIDADR: UN 3272 3/PG 3
WGK Germany: 3
HazardClass: 3
PackingGroup: III

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