Dimethyl Sulfoxide → 1-(Diphenylmethyl)azetidin-3-one

Participants

Reaction Steps

To a stirred solution of oxalyl chloride (21.6 g, 170 mmol) in CH2Cl2 (270 mL) was added DMSO (26.6 g, 340 mmol) at −78° C. Then to the mixture was added dropwise a solution of 1-benzhydryl-3-azetidinol (13.6 g, 56.7 mmol) in CH2Cl2 (68 mL). After the mixture was stirred for 30 min, to the mixture was added triethylamine (51.6 g, 510 mmol) at −78° C., and the resulting mixture was warmed to room temperature and stirred for 30 min before H2O (50 mL) was added. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 230-400 mesh, 300 g, Hexane/AcOEt=7/1 to 3/1) to give a product (10.0 g, 75%) as a yellow crystal.

Provenance & Evidence