2-(benzyloxy)-4-chloropyridine

26452-80-2

100-51-6

1006052-55-6

Potassium hydride (1.08 g, 27 mmol) was suspended in anhydrous tetrahydrofuran (80 mL) at 0 °C and protected by nitrogen, followed by the addition of benzyl alcohol (1.7 mL, 16.2 mmol) and the reaction was stirred for 1 hour. Next, a solution of 2,4-dichloropyridine (1.5 mL, 13.5 mmol) in tetrahydrofuran (5 mL) was added dropwise, and the reaction mixture was continued to be stirred at room temperature for 18 hours. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride solution (20 mL) and the organic solvent was removed by distillation under reduced pressure. The product was extracted from the remaining aqueous layer with dichloromethane (3 x 50 mL), the organic phases were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (petroleum ether/ether 8:2) to afford 2-(benzyloxy)-4-chloropyridine (Compound 7) as a light yellow oil (2.58 g, 87% yield); thin layer chromatography Rf = 0.56 (petroleum ether/ether 8:2).1H NMR (300 MHz, CDCl3) δ 5.46 (s, 2H), 6.87-6.89 ( m, 2H), 7.33-7.52 (m, 5H), 8.09 (dd, 1H, J = 4.7, 1.8 Hz).