Ethanol → 2-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid

HRID 1689195노트

반응식

HRID 1689195 반응식
[Si]([O:8][CH2:9][CH2:10][C:11]1[S:15][C:14](CC#N)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[OH-:19].[K+].[CH2:21]([OH:23])[CH3:22]>O>[OH:23][CH2:21][CH2:22][C:14]1[S:15][C:11]([CH2:10][C:9]([OH:8])=[O:19])=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 579893012-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetonitrile

생성물 1

HCID 579889872-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A solution of 2-(5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetonitrile (example 4, step d) (3 g) in ethanol (30 mL) was added to a stirred solution of potassium hydroxide (1.20 g) in water (30 mL). The resulting mixture was stirred at 100° C. for 4 hours. The reaction was concentrated in vacuo and the resulting mixture was partitioned between brine and ethyl acetate. The aqueous layer was cooled with ice, acidified by dropwise addition of concentrated hydrochloric acid and extracted with ethyl acetate three times. The combined organic solutions were washed with brine, dried over sodium sulphate, filtered and the solvent evaporated in vacuo to give the subtitled compound as a yellow solid.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resulting mixture was partitioned between brine and ethyl acetate
  3. temperatureThe aqueous layer was cooled with ice
  4. additionacidified by dropwise addition of concentrated hydrochloric acid
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic solutions were washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-46be980dcec04ed4b319d755fe3704f0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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