Imidazole → 4-((Tert-butyldimethylsilyl)oxy)but-2-yn-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 175 g of tert-butyldimethylsilyl chloride in 100 ml of a 1:1 mixture of hexane and dimethylformamide is slowly added in drops to a solution of 100 g of 2-butin-1-ol and 158 g of imidazole in 300 ml of dimethylformamide at 0° C. under nitrogen, and it is stirred for 2 hours at 0° C. and for 16 hours at 22° C. The reaction mixture is diluted with 2.5 l of ether, washed once with water, once with 5% sulfuric acid, once with water, once with saturated sodium bicarbonate solution and washed neutral with semi-saturated sodium chloride solution. After drying on sodium sulfate and filtration, it is concentrated by evaporation in a vacuum. The residue that is thus obtained is purified by chromatography on silica gel. 74.3 g of the title compound is obtained with hexane/0-40% ether as a colorless oil.

Provenance & Evidence