Methanol → N-(3-phenylcyclobutylidene)hydroxylamine

Participants

Reaction Steps

A yellow slurry of 3-phenylcyclobutanone (1.09 g, 7.44 mmol), MeOH (33.8 mL), water (3.38 mL), potassium carbonate (2.26 g, 16.4 mmol), and hydroxylamine hydrochloride (1.14 g, 16.4 mmol) was heated at 50° C. for 14 hours. The mixture was diluted with EtOAc (50 mL), washed with water (10 mL) and brine (10 mL), dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (0-50% EtOAc/hexanes, gradient elution) to provide the title compound (947 mg, 5.87 mmol, 79% yield). MS (DCI) M/Z 162 [M+H]+.

Provenance & Evidence