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Ethyl 2-oxo-4-phenylbutyrate

Ethyl 2-oxo-4-phenylbutyrate Basic information
synthesis
Product Name:Ethyl 2-oxo-4-phenylbutyrate
Synonyms:4-PHENYL-2-OXOBUTYRIC ACID ETHYL ESTER;2-OXO-4-PHENYLBUTANOIC ACID ETHYL ESTER;2-OXO-4-PHENYLBUTYRIC ACID ETHYL ESTER;BENZYLPYRUVIC ACID ETHYL ESTER;KETO ESTER;ETHYL BENZYLPYRUVATE;ETHYL-2 OXO-4 PHENYL BUTANOATE;ETHYL 2-OXO-4-PHENYLBUTYRATE
CAS:64920-29-2
MF:C12H14O3
MW:206.24
EINECS:265-276-9
Product Categories:C12 to C63;Carbonyl Compounds;Intermediates of Sertraline;Pharmaceutical Intermediates;Aromatics;Esters;(intermediate of lisinopril );Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;1
Mol File:64920-29-2.mol
Ethyl 2-oxo-4-phenylbutyrate Structure
Ethyl 2-oxo-4-phenylbutyrate Chemical Properties
Boiling point 132 °C/2 mmHg (lit.)
density 1.091 g/mL at 25 °C (lit.)
refractive index n20/D 1.504(lit.)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Oil
color Colourless
BRN 2725083
CAS DataBase Reference64920-29-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 23-24/25-36/37-26
WGK Germany 3
MSDS Information
ProviderLanguage
Ethyl 2-oxo-4-phenylbutyrate English
SigmaAldrich English
ALFA English
Ethyl 2-oxo-4-phenylbutyrate Usage And Synthesis
synthesisPotassium tert-butoxide (4.3 g, 38.34 mmol) was added in 1 portion to a solution of the diester (8 g, 25.56 mmol) in toluene (80 mL) at 0 °C. After being stirred at the same temperature for 30 min, the reaction mixture was kept at room temperature overnight. Water (100 mL) was added, the phases were separated, and the aqueous phase was extracted with EtOAc (3 × 100 mL). The combined organic extracts  were dried and evaporated. The residue was purifified by flflash chromatography  eluting with EtOAc:light petroleum (1:9) to give 5.6 g (78%) of the keto-ester as an orange oil.
Chemical Propertieslight yellow oily liquid
UsesEthyl 2-oxo-4-phenylbutyrate may be used in the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate, an important chiral precursor for angiotensin-converting enzyme (ACE) inhibitor.
General DescriptionEthyl 2-oxo-4-phenylbutyrate is an aliphatic α-ketoester. Bioreduction of ethyl 2-oxo-4-phenylbutyrate is reported to yield ethyl (R)-2-hydroxy-4-phenylbutanoate. The effect of ionic liquid on the asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae has been reported. Asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate using a bacterial reductase is reported. Enantioselective hydrogenation of ethyl 2-oxo-4-phenylbutyrate using homogeneous Rh-diphosphine and heterogeneous Pt/Al2O3-cinchona catalysts has been reported.
Ethyl 2-oxo-4-phenylbutyrate Preparation Products And Raw materials
Preparation ProductsEnalapril-->Spirapril-->Benzenebutanoic acid, a-hydroxy-, methyl ester-->N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine-->ETHYL (S)-2-HYDROXY-4-PHENYLBUTYRATE-->Ethyl (R)-2-hydroxy-4-phenylbutyrate
2-Phenylphenol Ethyl butyrate Ethyl 2-oxo-4-phenylbutyrate Ethanol ETHYL 4-(2-CHLOROPHENYL)-2,4-DIOXOBUTANOATE ethyl 4-(2,4-dimethylphenyl)-2,4-dioxobutanoate Phenylacetone ethyl 4-(2,4-dichlorophenyl)-2,4-dioxobutanoate Ethylparaben ETHYL 4-(3-NITROPHENYL)-2,4-DIOXOBUTANOATE ethyl 4-(2,4-difluorophenyl)-2,4-dioxobutanoate ETHYL 2-KETO-4-PHENYL-D5-BUTANOATE ETHYL 2,4-DIOXO-4-PHENYLBUTANOATE AKOS MSC-0265 Ethyl vanillin Ethyl acrylate Triphenylphosphine Ethyl 4'-hydroxy-3'-methoxycinnamate
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