Acetaldehyde → 1-(6-Methoxypyridin-3-yl)ethanol

Participants

Reaction Steps

To a solution of 5-bromo-2methoxy-pyridine (19.3 g, 193 mmol) in anhydrous Et2O (200 mL) at −78° C. was added n-BuLi (2.5 M in hexanes, 50 mL) over 30 min. The resulting mixture was stirred at that temperature for addition 30 min before acetaldehyde (5 mL) was added. The reaction was slowly warmed up to room temperature and the solvent was removed in vacuo. The residue was purified by flash column chromatography to afford the desired product (14.3 g, 91% yield). 1H NMR (400 MHz, CDCl3): δ 1.50 (d, J=8.0 Hz, 3 H), 3.93 (s, 3 H), 4.87–4.92 (m, 1 H), 6.75 (d, J=8.0 Hz, 3 H), 7.63–7.66 (m, 1 H), 8.12–8.14 (m, 1 H).

Provenance & Evidence