Imidazole → ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate

HRID 1901197노트

반응식

HRID 1901197 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:9]([O:19][CH2:20][CH3:21])(=[O:18])[C@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11].N1C=CN=C1>CN(C)C=O>[Si:1]([O:11][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([O:19][CH2:20][CH3:21])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6951557ethyl mandelate, (S)-

생성물 1

HCID 10968419ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
40 °C

실험 절차

A solution of 31.4 g of t-butyldimethylsilyl chloride in 200 ml of dimethylformamide was added dropwise to a solution of 25 g of ethyl (S)-(+)-mandelate and 28.4 g of imidazole in 800 ml of dimethylformamide, and the resulting mixture was stirred overnight at 40° C. At the end of this time, the dimethylformamide solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give the title compound having an Rf=0.84 (thin layer chromatography over silica gel, using a 10:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

후처리

  1. customAt the end of this time, the dimethylformamide solvent was removed by distillation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-a8a55a2b31974336a352f45844f78ef6
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576340

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