Water → 5-Methoxy-2-methylpyridine

Participants

Reaction Steps

5-Hydroxy-2-methylpyridine (15 g, 0.14 mol) was added to a stirred suspension of KOH (31 g, 0.55 mol) in DMSO (150 mL). The mixture was stirred for 1 hour and then treated with methyl iodide (9.8 mL, 0.15 mol). After 20 mins the reaction mixture was poured into H2O and extracted with ether. The ether extracts were dried over MgSO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 50% EtOAc in hexanes) gave the product as a clear oil (10.1 g, 59%). 1H NMR (400 MHz, CDCl3): δ 2.49 (s, 3 H), 3.83 (s, 3 H), 7.06 (d, J=8.6 Hz, 1 H), 7.12 (d, J=8.3 Hz, 1 H), 8.19 (d, J=2.8 Hz, 1 H).

Provenance & Evidence