Imidazole → 4-[2-(Tert-butyldiphenylsilyloxy)ethyl]nitrobenzene

Participants

Reaction Steps

A solution containing 3 g (18 mmol) of 4-nitrophenethyl alcohol, 5.2 ml (20 mmol) of tert-butylchlorodiphenylsilane, 3.05 g (45 mmol) of imidazole and 438 mg (3.5 mmol) of N,N-dimethylaminopyridine in dimethylformamide (20 ml) was stirred under a nitrogen atmosphere at room temperature for 3 hours. The solvent was evaporated and the residue partitioned between ethyl acetate (40 ml) and 2M hydrochloric acid (40 ml). The ethyl acetate layer was separated, washed with saturated aqueous sodium bicarbonate (40 ml), dried over magnesium sulfate, filtered and evaporated to give 6.56 g of 4-[2-(tert-butyldiphenylsilyloxy) ethyl]nitrobenzene as a yellow gum.

Provenance & Evidence