Imidazole → 4-((tert-Butyldimethylsilyl)oxy)butan-2-ol

Participants

Reaction Steps

In N,N-dimethylformamide (30 ml) was dissolved 1,3-butanediol (3.00 g, 33.3 mmol), followed by the dropwise addition of an N,N-dimethylformamide solution (30 ml) of imidazole (2.72 g, 40.0 mmol) and t-butylchlorodimethylsilane (5.29 g, 35.0 mmol). After stirring at room temperature for 24 hours, ether was added to the reaction mixture and the white solid thus precipitated was filtered off. The resulting ether solution was washed with water and brine, dried over magnesium sulfate and then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=5:1 eluate was concentrated, whereby the title compound (5.43 g, 26.6 mmol, 80%) was obtained as a colorless oil.

Provenance & Evidence