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

HRID 1901197Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-a8a55a2b31974336a352f45844f78ef6
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576340

Reaction notes

Loading…