ethyl acetoacetate
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With (S)-4,12-bis(diphenylphosphino)-<2.2>paracyclophane-Ru(II)bis(trifluoroacetate); hydrogen; tetra-(n-butyl)ammonium iodide In methanol; water at -5℃; under 2585.7 Torr; for 18h; | 100% |
With hydrogen; Ru(R-Xyl-P-Phos)(C6H6)Cl2 In ethanol; dichloromethane at 70℃; under 10343 Torr; for 1h; | 100% |
With [(+)-N,N'-Me2-3,3'-(Ph2P)2-1,1'-biindole]RuCl2; hydrogen In methanol; water at 45℃; under 79805.4 Torr; for 0.5h; | 100% |
ethyl 3-hydroxybutyrate
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With alcohol dehydrogenase from Thermoanaerobium brockii; NADH-specific (R)-selective-ADH; YcnD-oxidoreductase at 30℃; for 24h; pH=7.5; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction; | 99% |
(R)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sodium perborate In tetrahydrofuran; water at 20℃; | 94% |
With sodium peroxoborate tetrahydrate In tetrahydrofuran; water at 20℃; for 3h; | 84% |
With sodium perborate tetrahydrate In tetrahydrofuran; water Inert atmosphere; |
ethyl acetoacetate
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (S)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With citrate-phosphate-borate buffer for 24h; Ambient temperature; baker's yeast immobilized in calcium alginate; Title compound not separated from byproducts; | A n/a B 85% |
With Convolvulus sepium for 120h; pH=5.8; aq. phosphate buffer; optical yield given as %ee; | A n/a B 70% |
yeast Conversion of starting material; Enzymatic reaction; | A n/a B 26% |
ethanol
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (3R)-hydroxyvalerate
Conditions | Yield |
---|---|
With sulfuric acid In 1,2-dichloro-ethane for 48h; Heating; | A 84% B 59% |
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid In ethanol Heating; | 83% |
ethanol
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid In 1,2-dichloro-ethane Heating; | 82% |
ethanol
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid In 1,2-dichloro-ethane for 75h; Reflux; | 81% |
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; 1,2-dichloro-ethane for 37h; Heating; Irradiation; | 80% |
ethanol
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid In 1,2-dichloro-ethane for 96h; Heating; | 71% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; | 66% |
With sulfuric acid |
ethyl 4,4,4-trifluoroacetoacetate
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (3S)-4,4,4-trifluoro-3-hydroxybutanoate
C
ethyl (3R)-4,4,4-trifluoro-3-hydroxybutanoate
Conditions | Yield |
---|---|
With Fala baker' yeast; allyl alcohol Microbiological reaction; | A 62% B n/a C n/a |
ethanol
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid In 1,2-dichloro-ethane for 48h; | 60% |
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With trimethyltin(IV) hydroxide In 1,2-dichloro-ethane at 60℃; for 10h; Inert atmosphere; chemoselective reaction; | 58% |
ethyl acetoacetate
A
Ethyl (R)-3-hydroxybutanoate
B
3,3-bismethoxybutyric acid methyl ester
Conditions | Yield |
---|---|
With <(+)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzothiophene>RuCl2; hydrogen In methanol at 70℃; under 73550.8 Torr; for 2h; Yield given; | A n/a B 5% |
Conditions | Yield |
---|---|
With sulfuric acid |
ethyl 3-hydroxybutyrate
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (S)-3-hydroxybutyrate
Conditions | Yield |
---|---|
Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With pentyl cage-coated capillary column Resolution of racemate; | |
With homochiral metal-organic cage [Zn3(deprotonated [3+3] macrocyclic Schiff base of trans-1,2-diaminocyclohexane and 4-tert-butyl-2,6-diformylphenol)2] coated capillary column In dichloromethane at 118℃; Resolution of racemate; enantioselective reaction; |
ethyl acetoacetate
A
(S)-3-Hydroxybutanoic Acid
B
(R)-3-hydroxybutyric acid
C
Ethyl (R)-3-hydroxybutanoate
D
ethyl (S)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With Halobacterium halobium; pepton; potassium chloride; water; sodium citrate; magnesium sulfate; sodium chloride at 40℃; for 120h; Irradiation; Yields of byproduct given. Title compound not separated from byproducts; | |
With Halobacterium halobium; pepton; potassium chloride; sodium citrate; magnesium sulfate; sodium chloride In water at 40℃; for 120h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
ethyl 3-nitro-oxy-butanoate
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (S)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
ethyl (S)-3-hydroxybutyrate
N,N-dimethyl-formamide
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid 2.) MeOH, 1 h, room temperature; Yield given; |
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sodium tetrahydroborate; hydrogen; nickel dichloride for 16h; Ambient temperature; Yield given; |
ethanol
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid |
ethanol
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With sulfuric acid 1.) 1,2-dichloroethane, reflux, 2 h; 2.) reflux, 48 h; Yield given. Multistep reaction; |
ethyl 4,4,4-trifluoroacetoacetate
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (3S)-4,4,4-trifluoro-3-hydroxybutanoate
C
ethyl acetoacetate
D
ethyl (3R)-4,4,4-trifluoro-3-hydroxybutanoate
Conditions | Yield |
---|---|
With Fala baker' yeast; allyl alcohol |
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol In 1,2-dichloro-ethane for 12h; Heating; | 0.93 g |
ethanol
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (3R)-hydroxyvalerate
Conditions | Yield |
---|---|
Stage #1: poly[(R)-hydroxybutyrate] BIOPOL D300G In dichloromethane at 83℃; for 2h; Stage #2: ethanol With sulfuric acid In dichloromethane for 71h; Heating; Title compound not separated from byproducts; |
trans-Crotonaldehyde
ethanol
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (S)-3-hydroxybutyrate
Conditions | Yield |
---|---|
Stage #1: trans-Crotonaldehyde; ethanol With dihydrogen peroxide In chloroform at -20℃; for 16h; Stage #2: With N-ethyl-N,N-diisopropylamine In chloroform at 30℃; for 15h; Further stages. Title compound not separated from byproducts.; |
ethyl (S)-3-tosyloxy-butanoate
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / (n-Bu4)N(1+)*NO3(1-) / benzene / 6 h / Heating 2: H2 / Pd/C / methanol View Scheme |
acetylacetone
A
Ethyl (R)-3-hydroxybutanoate
B
ethyl (S)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With D-glucose In phosphate buffer at 30℃; for 12h; pH=7; Title compound not separated from byproducts.; |
Ethyl (R)-3-hydroxybutanoate
tert-butyldimethylsilyl chloride
ethyl (R)-3-[(tert-butyldimethylsilyl)oxy]butanoate
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; | 100% |
With 1H-imidazole In dichloromethane | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 100% |
Ethyl (R)-3-hydroxybutanoate
ethyl vinyl ether
Conditions | Yield |
---|---|
trifluoroacetic acid | 100% |
3,4-dihydro-2H-pyran
Ethyl (R)-3-hydroxybutanoate
(3R,2'RS)-3-<(Tetrahydropyran-2'-yl)oxy>buttersaeure-ethylester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 0.25h; | 100% |
With toluene-4-sulfonic acid In diethyl ether | 100% |
With pyridinium p-toluenesulfonate In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; Schlenk technique; | 91% |
With toluene-4-sulfonic acid |
Ethyl (R)-3-hydroxybutanoate
tert-butylchlorodiphenylsilane
(R)-3-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde
Conditions | Yield |
---|---|
Stage #1: Ethyl (R)-3-hydroxybutanoate; tert-butylchlorodiphenylsilane With 1H-imidazole; dmap In dichloromethane Stage #2: With diisobutylaluminium hydride In dichloromethane at -78℃; Further stages.; | 100% |
Ethyl (R)-3-hydroxybutanoate
ethyl vinyl ether
ethyl-3-(1-ethoxyethoxy)-butanoate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 1h; Ambient temperature; | 99% |
Ethyl (R)-3-hydroxybutanoate
tert-butylchlorodiphenylsilane
ethyl (R)-3-(tert-butyldiphenylsilyloxy)butyrate
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide | 99% |
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide for 72h; Ambient temperature; | 96% |
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Ambient temperature; | 95% |
With 1H-imidazole In dichloromethane at 0 - 20℃; for 6h; | 80% |
Ethyl (R)-3-hydroxybutanoate
methanesulfonyl chloride
(-)-(R)-Ethyl 3-(mesyloxy)butanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 99% |
With triethylamine In dichloromethane at 0℃; for 1h; | 97% |
With triethylamine In dichloromethane | 75% |
Conditions | Yield |
---|---|
scandium tris(trifluoromethanesulfonate) at 64℃; for 10h; | 98% |
(EtO)3TiO(CH2)2OTi(OEt)3 autoclave, 1.) 160 deg C, 17 bar, 2 h; 2.) 115 deg C, 3.5 bar, 27 h; | 82% |
Ethyl (R)-3-hydroxybutanoate
triethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 18h; | 96% |
With 1H-imidazole In dichloromethane |
Ethyl (R)-3-hydroxybutanoate
p-toluenesulfonyl chloride
(-)-(R)-Ethyl 3-<(p-tolylsulfonyl)oxy>butanoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; for 12h; | 95% |
With pyridine In chloroform at 0℃; for 12h; | 71% |
With pyridine at 0℃; for 24h; | 22.1 g |
Ethyl (R)-3-hydroxybutanoate
t-butyldimethylsiyl triflate
ethyl (R)-3-[(tert-butyldimethylsilyl)oxy]butanoate
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 2.5h; | 95% |
With pyridine In dichloromethane at 0 - 20℃; | 62% |
With pyridine Etherification; |
Ethyl (R)-3-hydroxybutanoate
chloromethyl methyl ether
(R)-ethyl 3-(methoxymethoxy)butanoate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 95% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Etherification; | 86% |
With N-ethyl-N,N-diisopropylamine In dichloromethane | 75% |
Ethyl (R)-3-hydroxybutanoate
methyl 3'-(cyanocarbonyl)-2,2'-binaphthalene-3-carboxylate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; for 2h; | 95% |
Ethyl (R)-3-hydroxybutanoate
methyl iodide
ethyl anti-(2R,3R)-2-methyl-3-hydroxybutanoate
Conditions | Yield |
---|---|
Stage #1: Ethyl (R)-3-hydroxybutanoate With n-butyllithium; diisopropylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - -40℃; for 0.333333h; Frater-Seebach alkylation; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 0℃; Frater-Seebach alkylation; Inert atmosphere; enantioselective reaction; | 94% |
Stage #1: Ethyl (R)-3-hydroxybutanoate With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - -40℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 0℃; for 2h; Inert atmosphere; | 92% |
With lithium diisopropyl amide In tetrahydrofuran at -78℃; | 84% |
Ethyl (R)-3-hydroxybutanoate
(R)-3-hydroxybutyric acid
Conditions | Yield |
---|---|
With potassium hydroxide at 0℃; for 24h; | 93% |
With sodium hydroxide In water at 10℃; for 6h; | 85% |
With potassium hydroxide for 12h; Ambient temperature; |
(η5-C5H4CH3)3Pr
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
In toluene N2-atmosphere; equimolar amts., -70°C; elem. anal.; | 93% |
Ethyl (R)-3-hydroxybutanoate
(2-trimethylethylsilylethoxy)methyl chloride
Ethyl (3R)-3-{[2-(trimethylsilyl)ethoxy]methoxy}butanoate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; | 93% |
3,4-dihydro-2H-pyran
Ethyl (R)-3-hydroxybutanoate
ethyl (R)-β-tetrahydropyranyloxybutyrate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 3h; Ambient temperature; | 92.5% |
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 90℃; for 16h; Inert atmosphere; | 92% |
With hydrazine hydrate In ethanol at 90℃; for 16h; | 92% |
With hydrazine hydrate In ethanol; water Reflux; | 1.95 g |
Ethyl (R)-3-hydroxybutanoate
potassium (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With potassium hydroxide In water at 10℃; for 5h; | 88.2% |
Ethyl (R)-3-hydroxybutanoate
benzylamine
(R)-N-benzyl-3-hydroxybutanamide
Conditions | Yield |
---|---|
Stage #1: benzylamine With trimethylaluminum In toluene at -5 - 20℃; Stage #2: Ethyl (R)-3-hydroxybutanoate In toluene at -5 - 20℃; for 15.5h; | 88% |
Ethyl (R)-3-hydroxybutanoate
O-(4-methoxybenzyl)-trichloroacetimidate
(R)-3-(4-Methoxy-benzyloxy)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With (1S)-10-camphorsulfonic acid In dichloromethane for 25h; Ambient temperature; | 86% |
Ethyl (R)-3-hydroxybutanoate
(R)-butane-1,3-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 1h; Ambient temperature; | 86% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.5h; | 85.6% |
Stage #1: Ethyl (R)-3-hydroxybutanoate With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: With water In diethyl ether | 81% |
Ethyl (R)-3-hydroxybutanoate
(2,6-dichloro-4-methoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidate
C20H20Cl4O4
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; | 85% |
Ethyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
Stage #1: Ethyl (R)-3-hydroxybutanoate With sodium hydroxide In water at 10℃; for 5h; Stage #2: With magnesium hydroxide In water for 10h; | 85% |
This chemical is called Butanoic acid, 3-hydroxy-, ethyl ester, (3R)-, and its CAS registry number is 24915-95-5. With the molecular formula of C6H12O3, its product categories are Alcohols, Hydroxy Esters and Derivatives; Chiral Compounds; Chiral Building Blocks; Simple Alcohols (Chiral); Synthetic Organic Chemistry; Chiral Building Blocks. In addition, this chemical should be sealed in the cool and dry place, away from oxides.
Other characteristics of the Butanoic acid, 3-hydroxy-, ethyl ester, (3R)- can be summarised as followings: (1)ACD/LogP: 0.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.098; (4)ACD/LogD (pH 7.4): 0.098; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 26.922; (8)ACD/KOC (pH 7.4): 26.922; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 46.53 Å2; (13)Index of Refraction: 1.427; (14)Molar Refractivity: 33.114 cm3; (15)Molar Volume: 128.941 cm3; (16)Polarizability: 13.128×10-24cm3; (17)Surface Tension: 33.285 dyne/cm; (18)Density: 1.025 g/cm3; (19)Flash Point: 64.444 °C; (20)Enthalpy of Vaporization: 47.888 kJ/mol; (21)Boiling Point: 174.999 °C at 760 mmHg; (22)Vapour Pressure: 0.362 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing to avoid contacting with skin and eyes. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1.SMILES: CCOC(=O)C[C@@H](C)O
2.InChI: InChI=1/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3/t5-/m1/s1
3.InChIKey: OMSUIQOIVADKIM-RXMQYKEDBL
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