Imidazole → 3-{[tert-Butyl(dimethyl)silyl]oxy}benzonitrile

Participants

Reaction Steps

To a solution of 3-cyanophenol (5 g, 42 mmol) and imidazole (6.3 g, 92 mmol) in N,N-dimethylformamide (85 mL) at 0° C. was added tert-butyldimethylsilylchloride (7.6 g, 50 mmol). After 10 min, the reaction was warmed to room temperature and stirred for 24 h. The solvent was removed under vacuum. The residual oil was diluted with water (100 mL) and extracted with ether (300 mL). The ether layer was back-extracted with water (3×100 mL) and brine (100 mL), dried (MgSO4) and filtered. Concentration and flash chromatography (silica, 50% ethyl acetate in petroleum ether) afforded 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzonitrile (9 g, 92%) as an oil.

Provenance & Evidence