Triethylamine → 1-(Diphenylmethyl)azetidin-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 1-diphenylmethyl-3-hydroxyazetidine (3.3 g, 14 mmol; J. Org. Chem. 1972, 37, 3953) in dimethyl sulphoxide (20 ml) was treated with triethylamine (19.2 ml), cooled to 15° C. and treated with sulphur trioxide pyridine (13.8 g) in dimethyl sulphoxide (30 ml), keeping the temperature below 20° C. The solution was stirred under an atmosphere of nitrogen at 15° C. for 45 minutes then at room temperature for 45 minutes. The solution was poured into ice water and extracted twice with ethyl acetate. The organic layer was collected, washed twice with water, dried (sodium sulphate), evaporated to dryness and the crude product purified using a plug of silica by eluting with dichloromethane to afford the ketone as a gum (2.9 g, 89%), δ (360 MHz, CDCl3) 4.00 (4H, s), 4.59 (1H, s), 7.12-7.49 (10H, m).

Provenance & Evidence