Imidazole → tert-Butyl(dimethyl)[(6-phenylhexyl)oxy]silane

Participants

Reaction Steps

The procedure used was similar to that described by Corey and Venkateswarlu (Corey, E. J.; Venkateswarlu, A., J. Am. Chem. Soc., 1972, 94, 6190-6191). 6-Phenyl-1-hexanol (14.0 g) and imidazole (13.36 g) were dissolved in dry DMF (40 mL). tert-Butyldimethylsilyl chloride (14.20 g,) was then added in one portion. The resulting solution was allowed to stir for 8 hours at room temperature. Aqueous sodium bicarbonate (100 mL, 10% by wt.) was then added and the resulting solution was allowed to stir for 15 minutes. The desired product was then extracted from the mixture with petroleum ether (3×250 mL). The petroleum ether extract was then washed with distilled H2O (7×300 mL), dried over MgSO4 and roto-evaporated to give the desired product as a clear oil.

Provenance & Evidence