Imidazole → 2-(tert-Butyl-dimethyl-silanyloxy)-ethoxyl-ethanol

Participants

Reaction Conditions

Reaction Steps

A solution of imidazole (2.11 grams, 31 mmol) and diethylene glycol (5 grams, 47 mmol) in dry DMF (11 ml) was cooled to 0° C. and stirred for 30 minutes under argon atmosphere. A solution of tert-butyldimethylsilyl chloride (4.72 grams, 31 mmol) in dry DMF (15 ml) was added dropwise and the resulting mixture was maintained for 2 hours at 0° C. and was then allowed to warm up to room temperature. Water (180 ml) was thereafter added and the resulting solution was extracted with ethyl acetate (4×80 ml). The combined organic extracts were washed with brine, the solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography, using ethyl acetate as eluent, to give the product (Compound 28a) as a white oil (4.65 grams, 45% yield).

Provenance & Evidence