Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at -10 - 10℃; for 2h; Inert atmosphere; | 94.9% |
With potassium carbonate In ethanol; water at 70℃; for 10h; regioselective reaction; | 85.3% |
With sodium ethanolate | 78% |
Conditions | Yield |
---|---|
With sodium In tetrahydrofuran for 20h; Heating; | 87% |
Stage #1: ethyl acetoacetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: ethyl iodide In tetrahydrofuran at 70℃; for 12h; Further stages.; | 74% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 3h; Ambient temperature; | 50% |
ethyl acetoacetate
ethyl iodide
A
ethyl 2,2-diethyl-3-oxobutanoate
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With P(MeNCH2CH2)3N In hexane; acetonitrile at 0℃; for 0.5h; | A n/a B 78% |
With sodium ethanolate 1.) EtOH, 80 deg C, 2.) EtOH, 80 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; | |
With aluminum oxide; sodium ethanolate 2.) room temperature, 5 d; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With sodium ethanolate 1.) EtOH, 80 deg C, 2.) EtOH, 80 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With dimethyl amine at 10 - 15℃; | 70% |
With sodium ethanolate |
diethyl sulfate
A
ethyl (Z)-3-ethoxybut-2-enoate
B
ethyl (E)-3-ethoxy-2-butenoate
C
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With polymer-HMPT In tetrahydrofuran at 20℃; for 24h; Yields of byproduct given; | A n/a B 54% C n/a |
With copolymere de vinyloxazolidone et de divinylbenzene In tetrahydrofuran at 20℃; for 24h; Yield given. Yields of byproduct given; | |
With 3-methyl-2-oxo-1,3-oxazolidine In tetrahydrofuran at 20℃; for 24h; Yield given. Yields of byproduct given; | |
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 20℃; for 24h; Product distribution; further reagents, variation of equivalents of the reagents; |
ethyl bromide
ethyl acetoacetate
A
ethyl 3-ethoxy-2-butenoate
B
ethyl 2,2-diethyl-3-oxobutanoate
C
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With aluminum oxide; sodium ethanolate 2.) room temperature, 5 d; Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 53% |
ethyl acetoacetate
diphenylethylsulfonium perchlorate
A
ethyl 3-ethoxy-2-butenoate
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane for 17h; Ambient temperature; | A 10% B 50% |
ethyl-α-ethylacetoacetate cyanohydrin
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol; ammonium hydroxide at 20℃; under 2068.59 - 2327.17 Torr; | A 50% B n/a |
ethyl bromide
18-crown-6 ether
acetoacetic acid ethyl ester; potassium (Z)-enolate
[2.2.2]cryptande
A
ethyl (Z)-3-ethoxybut-2-enoate
B
ethyl (E)-3-ethoxy-2-butenoate
C
ethyl 2,2-diethyl-3-oxobutanoate
D
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 40℃; Mechanism; Product distribution; | A 2% B 8% C n/a D n/a |
Conditions | Yield |
---|---|
bei der Ozonspaltung; |
4-ethyl-3-methyl-pentenedioic acid diethyl ester
A
oxalic acid
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
bei der Ozonspaltung; |
2-acetyl-3-methyl-succinic acid-1-ethyl ester
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
Erhitzen; |
ethanol
ethyl acetoacetate
ethyl iodide
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
Reaktion ueber mehrere Stufen; |
ethyl bromide
sodium ethanolate
ethyl acetoacetate
diethyl malonate
A
ethyl diethyl malonate
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
at 100℃; beim folgenden Kochen mit Wasser; | |
anschliessende Hydrolyse des Reaktionsprodukts mit siedendem Wasser; |
ethanol
sodium ethyl acetylacetate enolate
ethyl iodide
ethyl 2-ethyl-3-oxobutanoate
3-diethylamino-crotonic acid ethyl ester
ethyl iodide
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
anschliessende Hydrolyse des Reaktionsprodukts mit siedendem Wasser; |
sodium ethyl acetylacetate enolate
ethyl iodide
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
at 160 - 170℃; | |
With diethyl ether | |
With benzene | |
at 100℃; |
sodium ethanolate
ethyl iodide
acetoacetic acid methyl ester
ethyl 2-ethyl-3-oxobutanoate
ethyl iodide
3-dimethylamino-crotonic acid ethyl ester
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
anschliessenden Hydrolyse mit Wasser; | |
anschliessende Hydrolyse des Reaktionsprodukts mit siedendem Wasser; |
ethyl acetate
2-bromobutyric acid ethyl ester
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With magnesium |
Conditions | Yield |
---|---|
With diethyl ether; iodine; zinc |
ethyl bromide
ethyl acetoacetate
A
ethyl 3-ethoxy-2-butenoate
B
ethyl 2,2-diethyl-3-oxobutanoate
C
2-Ethyl-3-ethoxy-3-methyl-acrylsaeureethylester
D
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
(i) K, EtOH, (ii) /BRN= 1209224/, HMPA; Multistep reaction; |
ethyl bromide
acetoacetic acid ethyl ester; potassium (Z)-enolate
A
ethyl (Z)-3-ethoxybut-2-enoate
B
ethyl (E)-3-ethoxy-2-butenoate
C
ethyl 2,2-diethyl-3-oxobutanoate
D
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With 18-crown-6 ether 1) DME, 40 deg C, 2) DME, 40 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
ethyl bromide
acetoacetic acid ethyl ester; potassium (Z)-enolate
A
ethyl (E)-3-ethoxy-2-butenoate
B
ethyl 2,2-diethyl-3-oxobutanoate
C
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With [2.2.2]cryptande 1) t-BuOH, 40 deg C, 2) t-BuOH, 40 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
diethyl sulfate
C12H34N6O2P2*2C6H9O3(1-)*2Li(1+)
A
ethyl 3-ethoxy-2-butenoate
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
In dichloromethane for 72h; Product distribution; Ambient temperature; other metal ion, other time, var. addends; | A 46 % Chromat. B 54 % Chromat. |
diethyl sulfate
acetoacetic acid ethyl ester; potassium (Z)-enolate
A
ethyl (Z)-3-ethoxybut-2-enoate
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
In tetrahydrofuran for 66h; Yield given. Yields of byproduct given; | |
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 24h; Yield given. Yields of byproduct given; |
diethyl sulfate
enolate lithique de l'acetylacetate d'ethyle
A
ethyl (Z)-3-ethoxybut-2-enoate
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 74h; Yield given. Yields of byproduct given; | |
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 24h; Yield given. Yields of byproduct given; |
diethyl sulfate
enolate sodique de l'acetylacetate d'ethyle
A
ethyl (Z)-3-ethoxybut-2-enoate
B
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 120h; Yield given. Yields of byproduct given; | |
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 24h; Yield given. Yields of byproduct given; | |
With Hexamethylphosphorous triamide In tetrahydrofuran for 120h; Product distribution; Ambient temperature; different Li, Na, K enolates, ratios of reagent, reaction times; with solid and liquid and without HMPT; |
ethyl 2-ethyl-3-oxobutanoate
2-ethyl-2-chloro-acetoacetic acid ethyl ester
Conditions | Yield |
---|---|
With tetraethylammonium trichloride In dichloromethane | 100% |
With N-chloro-succinimide; magnesium(II) perchlorate In acetonitrile at 20℃; for 2h; | 86% |
With chlorine |
ethyl 2-ethyl-3-oxobutanoate
ethyl (2R,3S)-2-ethyl-3-hydroxybutanoate
Conditions | Yield |
---|---|
With D-glucose; ketoreductase-102; NADPH; glucose dehydrogenase; sodium phosphate buffer at 37℃; for 3h; pH=6.9; | 100% |
With D-glucose; calcium carbonate; sodium chloride In water at 35℃; for 72h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; | 78% |
With Escherichia coli strain expressing Gcy1p; isopropyl β-D-thiogalactopyranoside at 20℃; Reduction; | 75% |
With D-glucose; tris hydrochloride at 30℃; for 48h; β-keto ester reductase L-1, NADPH, GDH; | 31% |
With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate; baker yeast YDL124w gene-pIK8 plasmid; NAD at 30℃; for 24h; pH=7.0; |
[N-(p-tolylsulfonyl)imino]phenyliodinane
ethyl 2-ethyl-3-oxobutanoate
ethyl 2-acetyl-3-methyl-1-tosylaziridine-2-carboxylate
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 18h; Molecular sieve; Inert atmosphere; optical yield given as %de; | 99% |
ethyl 2-ethyl-3-oxobutanoate
4-ethyl-3-methylisoxazol-5(4H)-one
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol at 78℃; | 99% |
ethyl 2-ethyl-3-oxobutanoate
ethyl 2-bromo-2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With N-Bromosuccinimide; ammonium acetate In tetrachloromethane at 80℃; for 0.5h; | 97% |
With sodium hydrogen sulfate; N-Bromosuccinimide; silica gel at 20℃; for 2h; | 95% |
With ammonium bromide; dihydrogen peroxide; vanadia In dichloromethane; water at 0 - 5℃; for 3h; | 94% |
ethyl 2-ethyl-3-oxobutanoate
2-ethyl-1,3-butanediol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating; | 96% |
With methanol; copper chromite at 150 - 168℃; Hydrogenation.unter Druck; | |
With copper chromite; ethanol at 150 - 168℃; Hydrogenation.unter Druck; |
Conditions | Yield |
---|---|
Stage #1: N-hydroxyphthalimide; ethyl 2-ethyl-3-oxobutanoate With cobalt(II) diacetate tetrahydrate In acetic acid at 60℃; for 0.0166667h; Stage #2: With potassium permanganate In acetic acid at 60℃; for 0.175h; | 94% |
2-methylbenzene-1,3-diol
ethyl 2-ethyl-3-oxobutanoate
3-ethyl-7-hydroxy-4,8-dimethyl-2H-1-benzopyran-2-one
Conditions | Yield |
---|---|
With perchloric acid at 20℃; Pechmann condensation; | 92% |
With sulfuric acid at 0℃; for 12h; Pechmann Condensation; | |
With sulfuric acid at 0℃; Pechmann Condensation; |
ethylene glycol
ethyl 2-ethyl-3-oxobutanoate
2-ethoxycarbonylmethyl-2-methyl-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 120℃; for 4h; Product distribution / selectivity; | 91% |
With toluene-4-sulfonic acid In toluene at 120℃; for 4h; Heating / reflux; | 91% |
With toluene-4-sulfonic acid In toluene for 3.5h; Cyclization; Heating; | 70% |
phenylhydrazine
ethyl 2-ethyl-3-oxobutanoate
4-ethyl-3-methyl-1-phenylpyrazol-5-one
Conditions | Yield |
---|---|
for 0.05h; microwave irradiation; | 91% |
In ethanol Reflux; |
Conditions | Yield |
---|---|
With copper(II) acetate hydrate; 2-ethyl-1,3-oxazoline; copper(l) chloride In isopropyl alcohol at 20℃; regioselective reaction; | 90% |
ethyl 2-ethyl-3-oxobutanoate
3-methyl-4-ethyl-5-pyrazolone
Conditions | Yield |
---|---|
With hydrazine for 0.00833333h; | 89% |
With hydrazine hydrate; acetic acid In methanol at 100℃; for 1h; | 67% |
Conditions | Yield |
---|---|
ammonium cerium(IV) nitrate In ethanol at 20℃; for 1.5h; | 89% |
Conditions | Yield |
---|---|
With perchloric acid at 20℃; Pechmann condensation; | 89% |
2,2-dibromo-5,5-dimethylcyclohexane-1,3-dione
ethyl 2-ethyl-3-oxobutanoate
B
2-bromodimedone
Conditions | Yield |
---|---|
Stage #1: ethyl 2-ethyl-3-oxobutanoate With L-Norvaline In dichloromethane for 0.0833333h; Stage #2: 2,2-dibromo-5,5-dimethylcyclohexane-1,3-dione With dipyridinium dichromate In dichloromethane for 2h; Cooling with ice; optical yield given as %ee; enantioselective reaction; | A 88% B n/a |
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-ethyl-3-oxobutanoate With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Claisen Condensation; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.266667h; Claisen Condensation; Stage #3: ethyl (2S,3R)-3-(methoxymethyloxy)-2-methylbutanoate In tetrahydrofuran; hexane at 0℃; for 0.25h; Claisen Condensation; | 88% |
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-ethyl-3-oxobutanoate With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.266667h; Stage #3: ethyl (2R, 3S)-3-(methoxymethyloxy)-2-methylbutanoate In tetrahydrofuran; hexane at 0℃; for 0.25h; | 88% |
2-(4'-aminophenyl)-4-quinolinecarboxylic acid
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
Stage #1: 2-(4'-aminophenyl)-4-quinolinecarboxylic acid Stage #2: ethyl 2-ethyl-3-oxobutanoate With sodium hydroxide; sodium acetate In ethanol; water pH=4 - 4.5; Japp-Klingemann reaction; | 87% |
Conditions | Yield |
---|---|
ammonium cerium(IV) nitrate In ethanol at 20℃; for 3h; | 87% |
Conditions | Yield |
---|---|
Stage #1: 3-bromo-4-chloroaniline With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 1.16667h; Stage #2: ethyl 2-ethyl-3-oxobutanoate With potassium hydroxide In ethanol; water at 0 - 80℃; for 5h; pH=7; | 87% |
Stage #1: 3-bromo-4-chloroaniline With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: ethyl 2-ethyl-3-oxobutanoate With potassium hydroxide In ethanol; water at 0 - 80℃; for 5h; pH=7; | 87% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 24h; Ambient temperature; | 86% |
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
With N-iodo-succinimide; magnesium(II) perchlorate In acetonitrile at 20℃; for 0.25h; | 86% |
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide; sodium iodide In water; ethyl acetate at 0 - 5℃; for 13h; regioselective reaction; | 79% |
6-amino-4,7-dimethylcoumarin
ethyl 2-ethyl-3-oxobutanoate
Conditions | Yield |
---|---|
Stage #1: 6-amino-4,7-dimethylcoumarin With hydrogenchloride; acetic acid; sodium nitrite at 5℃; for 2h; Stage #2: ethyl 2-ethyl-3-oxobutanoate With sodium acetate; acetic acid at 20℃; for 10h; pH=5.5; | 86% |
N-(2-fluoro-3-nitrophenyl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide
ethyl 2-ethyl-3-oxobutanoate
ethyl (2E)-2-{[2-fluoro-3-({4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzoyl}amino)phenyl]hydrazono}butanoate
Conditions | Yield |
---|---|
Stage #1: N-(2-fluoro-3-nitrophenyl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide With hydrogen; palladium-on-charcoal In tetrahydrofuran; water at 20℃; for 15h; Stage #2: With hydrogenchloride; sodium nitrite In water; acetonitrile at -25 - 5℃; for 0.5h; Stage #3: ethyl 2-ethyl-3-oxobutanoate With potassium hydroxide In water at -20℃; | 86% |
methyl vinyl ketone
ethyl 2-ethyl-3-oxobutanoate
ethyl 2-ethyl-3-oxo-2-(3-oxo-1-butyl)-butanoate
Conditions | Yield |
---|---|
lithium hydroxide In 1,2-dimethoxyethane for 0.5h; Ambient temperature; | 85% |
lithium iodide In 1,4-dioxane for 12h; Heating; | 82% |
K bis(1,2-benzenediolato)phenylsilicate In chloroform at 40℃; for 6h; organosilicate-catalyzed Michael addition; | 74% |
With molecular sieve; Eu(tfc)3 In tetrachloromethane at -33℃; for 72h; | 71% |
With sodium perchlorate In methanol at 24.84℃; Michael Addition; Electrochemical reaction; |
ethyl 2-ethyl-3-oxobutanoate
ethyl 2-ethyl-2-chloro-3,3-difluorobutyrate
Conditions | Yield |
---|---|
With sulfur tetrafluoride; hydrogen fluoride; chlorine at 25℃; for 10h; autoclave; | 85% |
Conditions | Yield |
---|---|
Stage #1: ethyl 2-ethyl-3-oxobutanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: formaldehyd In tetrahydrofuran at -78 - 20℃; Further stages.; | 85% |
N,N-bis(ethoxymethyl)benzylamine
ethyl 2-ethyl-3-oxobutanoate
ethyl 1-benzyl-3-ethyl-4-oxo-3-piperidinecarboxylate
Conditions | Yield |
---|---|
With Methyltrichlorosilane In acetonitrile at 20℃; for 20h; Mannich reaction; | 85% |
Molecule structure of Butanoic acid,2-ethyl-3-oxo-, ethyl ester (CAS NO.607-97-6):
IUPAC Name: Ethyl 2-ethyl-3-oxobutanoate
Molecular Weight: 158.19496 g/mol
Molecular Formula: C8H14O3
Index of Refraction: 1.419
Molar Refractivity: 40.87 cm3
Molar Volume: 161.5 cm3
Surface Tension: 29.8 dyne/cm
Density: 0.979 g/cm3
Flash Point: 75.7 °C
Enthalpy of Vaporization: 42.62 kJ/mol
Boiling Point: 190 °C at 760 mmHg
Vapour Pressure: 0.554 mmHg at 25 °C
Storage Temp.: 2-8 °C
XLogP3-AA: 1.3
H-Bond Acceptor: 3
Rotatable Bond Count: 5
Tautomer Count: 5
Exact Mass: 158.094294
MonoIsotopic Mass: 158.094294
Topological Polar Surface Area: 43.4
Heavy Atom Count: 11
Canonical SMILES: CCC(C(=O)C)C(=O)OCC
InChI: InChI=1S/C8H14O3/c1-4-7(6(3)9)8(10)11-5-2/h7H,4-5H2,1-3H3
InChIKey: OKANYBNORCUPKZ-UHFFFAOYSA-N
EINECS: 210-151-6
Product Categories: Pharmaceutical Intermediates;Organic acids;API intermediates;C8 to C9;Carbonyl Compounds;Esters
Butanoic acid,2-ethyl-3-oxo-, ethyl ester (CAS NO.607-97-6) is used as intermediates for pharmaceutical.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-24/25-36-26
S23:Do not breathe vapour.
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 1
Butanoic acid,2-ethyl-3-oxo-, ethyl ester (CAS NO.607-97-6) is also named as AI3-06006 ; Ethyl 2-acetylbutyrate ; Ethyl 2-ethyl-3-ketobutyrate ; Ethyl 2-ethylacetoacetate ; Ethyl alpha-acetylbutyrate ; Ethyl alpha-ethylacetoacetate ; NSC 53775 ; Acetoacetic acid, 2-ethyl-, ethyl ester (8CI) .
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