GENERAL STEPS: Triethylamine (8.97 mL, 64.36 mmol) was added to a solution of dichloromethane (100 mL) containing 1-(hydroxymethyl)cyclopropane-1-carbonitrile (5 g, 51.48 mmol) and p-toluenesulfonyl chloride (11.78 g, 61.78 mmol), which was cooled to 0 °C under nitrogen protection. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction was quenched with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product as a white solid. The crude product was purified by fast silica gel column chromatography with an elution gradient of 0 to 100% petroleum ether solution in dichloromethane. The pure grades were collected and concentrated to dryness under reduced pressure to give (1-cyanocyclopropyl)methyl 4-methylbenzenesulfonate (5.20 g, 40% yield). LC/MS analysis: m/z = 252 [M + H]+. 1H NMR (300 MHz, CDCl3) δ 1.09 (dd, J = 7.5, 5.7 Hz, 2H), 1.38 (dd, J = 7.5, 5.4 Hz, 2H). 5.4 Hz, 2H), 2.48 (s, 3H), 4.01 (s, 2H), 7.40 (d, J = 8.1 Hz, 2H), 7.84 (d, J = 8.1 Hz, 2H).
