Thionyl Chloride → 2-Chloromethyl-4-(3-methoxypropoxy)pyridine

Participants

Reaction Steps

A solution of 2.60 g (0.022 mol) of thionyl chloride in 10 ml of chloroform was dropwise added to a solution of 3.64 g (0.018 mol) of 2-hydroxymethyl-4-methoxypropoxypyridine in 60 ml of chloroform under cooling with ice. The obtained mixture was stirred for one hour, neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with chloroform. The chloroform layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure to obtain 3.23 g of the title compound as a crude product. 1H-NMR (CDCl3) δ; 1.80~2.20 (m, 2H), 3.31 (s, 3H), 3.49 ((t, J=6.2 Hz, 2H), 4.07 (t, J=6.2 Hz, 2H), 4.55 (s, 2H), 6.52~6.96 (m, 2H), 8.26 (d, J=5.3 Hz, 1H)

Provenance & Evidence