Ethyl Acetate → tert-Butyl 3-oxocyclobutylcarbamate

Participants

Reaction Steps

To a solution of tert-butyl (3-methylidenecyclobutyl)carbamate (165 g, 0.91 mol) in CH2Cl2 (1000 mL) and MeOH (1000 mL) was bubbled O3 at −78° C. until the solution turned blue. TLC (petroleum ether:EtOAc=10:1) showed that the starting material was consumed completely. Nitrogen gas was then bubbled through the reaction to remove excess O3, and then the mixture was quenched with Me2S (200 mL) and stirred for an hour. The solution was concentrated to give a residue, which was washed with sat. NaHCO3 and water to yield the title compound (118 g, 70% yield) as a white solid.

Provenance & Evidence