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

Participants

Reaction Conditions

Reaction Steps

Dimethyl sulfoxide (0.36 mL, 5 mmol) was added dropwise to a stirred solution of oxalyl chloride (0.40 mL, 4.6 mmol) in dichloromethane (20 mL) at −78° C. under an argon atmosphere. The mixture was stirred for 10 minutes then a solution of 1-(diphenylmethyl)-3-azetidinol (1.0 g, 4.2 mmol) in dichloromethane (20 mL) was added dropwise. The mixture was warmed to −50° C. and sired for 30 minutes. Triethylamine (2.9 mL, 21 mmol) was added and the mixture warmed to room temperature. After 1 hour, water (50 mL) was added and the mixture extracted with dichloromethane (4×50 mL). The combined organic extracts were washed (brine), dried (Na2SO4) and concentrated in vacuo to give 1-diphenylmethyl-3-azetidinone (3) as a pale yellow crystalline solid (1.0 g, 99%) (lit. (S. S. Chattetjee and A. Shoeb, Synthesis, 1973,153) m.p. 82° C.).

Provenance & Evidence