Triethylamine → 5-Ethenyl-2-methoxypyridine

Participants

Reaction Steps

To a solution of 1-(6-methoxy-pyridin-3-yl)-ethanol (14.3 g, 93.5 mmol) in anhydrous THF was added triethylamine (32.3 mL), followed by MsCl (8.6 mL, 112 mmol). The resulting mixture was stirred at room temperature for 15 hours before it was filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography to afford the desired product (4.7 g, 37% yield). 1H NMR (300 MHz, CDCl3): δ 3.94 (s, 3 H), 5.20–5.23 (m, 1H), 5.61–5.67 (m, 1 H), 6.60–6.78 (m, 2 H), 7.67–7.72 (m, 1 H), 8.12 (s, 1 H).

Provenance & Evidence