Imidazole → 1-t-BUTYLDIPHENYLSILYLOXY-3-MERCAPTO-2-PROPANOL

Participants

Reaction Steps

To a solution of 3-mercapto-1,2-propanediol (5.00 g, 46.23 mmol) and imidazole (3.78 g, 55.47 mmol) in dimethylformamide (30 mL) was added t-butyldiphenylsilyl chloride (12.71 g, 46.23 mmol) at room temperature. After stirring for 18 h the reaction was quenched by the addition of saturated sodium bicarbonate and the mixture was extracted with ether (3X). The combined ether extracts were washed with water (2X), brine, dried and concentrated to give a yellow oil. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (90:10) to give the compound as a colorless oil (14.12 g) in 88% yield.

Provenance & Evidence