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

HRID 1901197ノート

反応式

HRID 1901197 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a8a55a2b31974336a352f45844f78ef6
出典データセット
uspto-grants-1996_11
特許番号
US05576340

反応ノート

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