tert-Butanol → tert-Butyl 3-butyn-1-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

Add triethylamine (3 mL) to a solution of 4-pentynoic acid (1.96 g, 20 mmol) in tert-butanol (6 mL) at 0° C. and then add diphenyl phosphoryl azide (CAUTION: reaction starts violently a short period after the addition). Heat the reaction mixture at 85° C. overnight under nitrogen. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with dichloromethane to obtain the title compound as a white solid (1.81 g, 53%).

Provenance & Evidence