Pyridine → (1-Cyanocyclopropyl)methyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of 1-(hydroxymethyl)cyclopropanecarbonitrile (1.0 g) in dichloromethane (15 ml) was added pyridine (4.1 ml) at 0° C., and the mixture was stirred at the same temperature for 15 min. To the obtained reaction mixture was added dropwise p-toluenesulfonyl chloride (3.9 g), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1 g).

Provenance & Evidence