Sodium Cyanide → N-(p-toluenesulfonyl)-3-(bromomethyl)4-(cyanomethyl)-3-pyrroline

Participants

Reaction Steps

10 g of N-(p-toluenesulfonyl)-3,4-bis(bromomethyl)-3-pyrroline, prepared in Preparation 5, was dissolved in 10 ml of dimethylsulfoxide (DMSO) and then heated in oil bath for 2 hours with refluxing. During the heating and refluxing, 1.5 g of sodium cyanide was added by small portion. The reaction mixture was cooled to room temperature and poured into ice water and then extracted with methylene chloride (200 ml×3). The extracts were combined, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography. 5 g of the title compound was obtained (yield 57%).

Provenance & Evidence