Imidazole → HCID 17947803, compound

Participants

Reaction Steps

A solution of tert-butyl 3-hydroxyphenylcarbamate (12-2, 6.40 g, 30.6 mmol, 1 equiv), t-butyldimethylsilyl chloride (4.61 g, 30.6 mmol, 1.00 equiv), and imidazole (2.71 g, 39.8 mmol, 1.30 equiv) in DMF (50 mL) was stirred at 23° C. for 16 h. The reaction mixture was partitioned between half-saturated sodium bicarbonate solution and ethyl acetate (200 mL). The organic layer was washed successively with half-saturated ammonium chloride solution (100 mL), saturated sodium bicarbonate solution (100 mL), and brine (100 mL), then dried over sodium sulfate and concentrated to give tert-butyl 3-{[tert-butyl(dimethyl)silyl]oxy}phenylcarbamate (12-3) as a white solid. 1H NMR (400 MHz, CDCl3) δ 6.92 (t, 1H, J=7.8 Hz), 6.73 (m, 2H), 6.31 (ddd, 1H, J=7.8, 1.9, 0.7 Hz), 6.20 br s, 1H), 1.32 (s, 9H), 0.78 (s, 9H), −0.02 (s, 6H).

Provenance & Evidence