Pyridine → HCID 131730048, compound

Participants

Reaction Conditions

Reaction Steps

A 250-mL, three-neck, round-bottomed flask equipped with a mechanical stirrer, a 50-mL pressure-equalizing addition funnel, an internal thermometer, and a nitrogen inlet was charged with chloroethyl chloroformate (10.8 g, 76 mmol) and 4-(methylthio)phenol (10 g, 71 mmol) in dichloromethane (75 mL). The resulting clear reaction mixture was cooled to 0° C. A solution pyridine (6.8 g, 86 mmol) in dichloromethane (10 mL) was slowly added over a period of 30 minutes. The reaction mixture was then stirred overnight at room temperature. The reaction mixture was poured into a separatory funnel, washed with water (100 mL), brine (100 mL), dried over sodium sulfate, and evaporated under vacuum to give the title compound D1 as a viscous oil (˜17 g, quantitative yield). 1H NMR (CDCl3, 400 MHz): δ 1.89 (d, J=6 Hz, 3H), 2.47 (s, 3H), 6.46 (q, J=6 Hz, 1H), 7.11 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.8 Hz, 2H).

Provenance & Evidence