Imidazole → 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

Participants

Reaction Steps

To a solution of 1,4-butanediol (4.0 g, 44.4 mmol) in 250 mL THF was added imidazole (3.7 g, 54.3 mmol) followed by tert-butyl(chloro)diphenylsilane (10 g, 36.4 mmol) at room temperature. The mixture was stirred for 3 h and then quenched by the addition of saturated aqueous NH4Cl (200 mL) and then diluted with ethyl acetate (200 mL). The mixture was extracted with ethyl acetate (3×200 mL) and the combined organic layers washed with brine (3×60 mL) and dried over Na2SO4. The solvent was evaporated and the product isolated by flash column chromatography eluting with 0 to 50% EtOAc/hexanes to give 10.6 g of the title compound as a colorless oil.

Provenance & Evidence