Sodium Methoxide → Ethanone, 1-(4-methoxy-3-pyridinyl)- (9CI)

Participants

Reaction Steps

A solution of 3-acetyl-4-chloropyridine (0.75 g, 4.8 mmol) in sodium methoxide solution (0.5M in methanol, 10.6 ml, 5.3 mmol) was heated at reflux for 1 hour. After cooling water (10 ml) was added and the solvents evaporated. The residue was partitioned between dichloromethane (4×50 ml) and water (50 ml), the combined organic phases dried (MgSO4) and evaporated to afford the title compound (0.58 g, 80%) as a yellow solid. 1H NMR (360 MHz, CDCl3) δ 2.62 (3H, s), 3.98 (3H, s), 6.90 (1H, d, J=5.8 Hz), 8.57 (1H, d, J=5.7 Hz), 8.81 (1H, s).

Provenance & Evidence