Water → 5-Methoxy-2-methylpyridine

Participants

Reaction Steps

To a suspension of potassium hydroxide (113 g, 2 mol) in DMSO (800 ml) was added 53.9 g, (0.49 mol) 5-hydroxy-2-methylpyridine and the mixture stirred for 1 h. To this was added CH3I (34 ml, 0.55 mol) and the reaction mixture was stirred for one hour, then poured into water (2400 ml) and extracted with ether (1000 ml×5). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo to provide 5-methoxy-2-methylpyridine as a yellow oil. 1H NMR: (400 MHz, CDCl3) δ 8.19 (d, J=2.8 Hz, 1H), 7.14 (dd, J=8.8, 3.8 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 3.83 (s, 3H), 2.65 (s, 3H).

Provenance & Evidence