tert-Butyldimethylsilyl chloride → N,N-diethyl-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-(trifluoromethoxy)benzamide

Participants

Reaction Steps

To a stirring solution of N,N-diethyl-4-hydroxy-2-(trifluoromethoxy)benzamide (1876 mg, 6.8 mmol) and diisopropylethylamine (1747 mg, 13.5 mmol) in dry DMF (60 mL) was added chloro(1,1-dimethylethyl)dimethylsilane (1123 mg, 7.5 mmol). The reaction was stirred for 16 h and then quenched with 1M HCl. The reaction was extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a pale yellow oil. The oil was purified by flash chromatography (silica gel, 0-40% EtOAc in hexanes) to give 1941 mg of the desired product as a colorless oil. MS (ESI) 392 (M+H).

Provenance & Evidence