2-Acetylthiophene → Rac-alpha-hydroxy-alpha-propyl-gamma-oxo-2-thiophenebutyric acid

HRID 1197806

반응식

HRID 1197806 반응식
[OH-].[K+].[CH3:3][CH2:4][CH2:5][C:6]([C:8]([OH:10])=[O:9])=[O:7].[C:11]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)(=[O:13])[CH3:12]>O.C(O)C>[OH:7][C:6]([CH2:5][CH2:4][CH3:3])([CH2:12][C:11](=[O:13])[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:8]([OH:10])=[O:9]

참가 물질

6

반응물 3

HCID 69202-AcetylthiopheneHCID 14797Potassium HydroxideHCID 745632-Oxovaleric acid

생성물 1

HCID 54564597Rac-alpha-hydroxy-alpha-propyl-gamma-oxo-2-thiophenebutyric acid수율 41.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

11.2 g (200 mmol) of potassium hydroxide in 75 ml of water are added at 0° dropwise to a suspension of 11.6 g (100 mmol) of 2-oxo-n-valeric acid and 12.6 g (100 mmol) of 2-acetylthiophene in 75 ml of ethanol and the suspension is held at 0° for 48 hours. After evaporation of the ethanol the residue is made acidic with 25% hydrochloric acid and extracted three times with ethyl acetate. The combined ethyl acetate extracts are dried, filtered and evaporated. After chromatography on silica gel using a 5:1 mixture of methylene chloride and methanol as the eluent and crystallisation from ether there are obtained 10.0 g (41%) of rac-α-hydroxy-α-propyl-γ-oxo-2-thiophenebutyric acid as a colorless powder, melting point 128°-131°, MS: 197 (M-COOH)+.

후처리

  1. customAfter evaporation of the ethanol the residue
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. additionAfter chromatography on silica gel using a 5:1 mixture of methylene chloride and methanol
  7. customas the eluent and crystallisation from ether

출처 및 근거

ORD 기록
ord-a9394a4307f54d3e8de32a04755f31c9
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278161

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