Citric Acid → Diethyl (1-benzhydryl-3-azetidinyl)malonate

Participants

Reaction Steps

To 17.90 g (111.80 mmol) of diethyl malonate dissolved in 250 ml of tetrahydrofuran was added 4.07 g (101.75 mmol) of 60% sodium hydride at room temperature, followed by 2 hours of stirring. Thereafter, thereto was added 20 g (50.82 mmol) of 1-benzhydryl-3-(p-toluenesulfonyloxy)azetidine which has been dissolved in 90 ml of tetrahydrofuran, followed by 1 week of heating under reflux. The reaction solution was mixed with 10% citric acid aqueous solution and then tetrahydrofuran was evaporated. The resulting residue was mixed with saturated sodium bicarbonate aqueous solution, extracted with chloroform (200 ml×3) and dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (230-400 mesh silica gel 450 ml, ethyl acetate:hexane 1:3) to yield quantitative amount of the title compound.

Provenance & Evidence