tert-Butanol → tert-butyl N-(5-methylthiophen-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methylthiophene-2-carboxylic acid (5 g, 35.2 mmol) in tert-butanol (99 mL) was added Et3N (3.91 g, 38.7 mmol) and diphenyl phosphoryl azide (10.65 g, 38.7 mmol). The reaction mixture was heated to 65° C. for 4 h, then refluxed for 4 h. The volatiles were removed under reduced pressure and the residual crude material was purified by flash chromatography on silica gel (DCM/MeOH: 98/2) to give the title compound (7 g, 75%): 1HNMR (DMSO) δ 10.10 (s, 1H), 6.43 (d, J=2 Hz, 1H), 6.29 (d, J=2 Hz, 1H), 2.30 (s, 3H), 1.42 (s, 9H).

Provenance & Evidence