Phosphoric Acid → 1-(Diphenylmethyl)azetidin-3-one

Participants

Reaction Steps

7.17 g (0.03 mole) of 1-benzhydryl-3-hydroxyazetidine were dissolved in a mixture of 35 ml of dimethyl sulfoxide and 20 ml of methylene chloride. 1 ml of pyridine, 0.5 ml of phosphoric acid and then 12.5 g (0.06 mole) of 1,3-dicyclohexylcarbodiimide were added, in turn, to the resulting solution. The reaction mixture was then stirred for 2 hours, after which water was added to it. The reaction mixture was then extracted twice, each time with 200 ml of chloroform. The combined extracts were dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The concentrate was subjected to silica gel column chromatography, and 4.84 g (67%) of 1-benzhydryl-3-oxoazetidine were obtained from the fractions eluted with a 9:1 by volume mixture of toluene and ethyl acetate.

Provenance & Evidence