Acetone → 1-(Pyridin-3-yl)butane-1,3-dione

Participants

Reaction Steps

To a solution of methylpyridine-3-carboxylate (20.0 g, 146 mmol) in THF (200 mL) was added acetone (50 mL, 681.0 mmol). Sodium methoxide (32.7 mL of 25% w/w, 146.0 mmol) was added dropwsie at rt under N2. The mixture was stirred at rt for 72 hours, quenched with sat. NH4Cl, acidifed with 1 N HCl to pH-5. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to dryness. The crude material was purified by column chromatography (0-10% EtOAc-Hex) to provide 1-(3-pyridyl)butane-1,3-dione (7 g) as a light yellow crystalline solid. 1H NMR (400 MHz, CDCl3) δ 15.98 (s, 1H), 9.19-8.99 (m, 1H), 8.74 (dd, J=4.8, 1.7 Hz, 1H), 8.34-8.04 (m, 1H), 7.41 (ddd, J=8.0, 4.8, 0.8 Hz, 1H), 6.20 (s, 1H), 2.24 (s, 3H). ESI-MS m/z calc. 163.06, found 164.3 (M+1)+; Retention time: 0.32 minutes (3 min run).

Provenance & Evidence