Pyridine →

Participants

Reaction Conditions

Reaction Steps

A solution of thietan-3-ol (450 mg) and Et3N (1 ml) in dichloromethane (3 ml) was added dropwise to over 30 minutes to a solution of p-toluenesulfonyl chloride (1 g) in dichloromethane (3 ml) at −10° C. under argon atmosphere. The yellow solution was stirred at −10° C. for 1 hour then pyridine (1 ml) was added, and the resulting red solution was stirred for 1 hour at −10° C. The precipitated solid was collected by filtration then washed with diethyl ether (3×5 ml) and dried under high vacuum to afford the title compound as a white solid (405 mg). MS (Method A) positive ion mass: 152 (3-pyridinium thietane), negative ion mass: 171 (p-toluenesulfonate). 1H-NMR (DMSO, 400 MHz): 2.30 (s, 3H), 3.57 (t, 2H), 4.09 (t, 2H), 6.16 (q, 1H), 7.12 (d, 2H), 7.50 (d, 2H), 8.20 (t, 2H), 8.66 (t, 1H), 9.21 (d, 1H).

Provenance & Evidence