Sodium Hydroxide → 2-Methoxy-6-methylpyridine

Trimethyloxonium tetrafluoroborate (10.0 g, 67.6 mmol) was added portionwise to a suspension of 6-methylpyridin-2-one (7.3 g, 67.0 mmol) in dichloromethane (100 ml), and once addition was complete, the reaction was stirred at room temperature for 24 hours. Dichloromethane (50 ml) and aqueous sodium hydroxide solution (50 ml, 2N) were added and the layers separated. The aqueous phase was extracted with dichloromethane (2×50 ml), the combined organic solutions washed with brine (50 ml), dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using an elution gradient of pentane: dichloromethane (66:34 to 0:100) to afford the title compound (2.25 g, 27%) as a colourless oil. δ (CDCl3): 2.49 (3H, s), 3.90 (3H, s), 6.38-6.73 (2H, m), 7.23-7.40 (1 H, br d).

1. customthe layers separated
2. extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
3. washthe combined organic solutions washed with brine (50 ml)
4. dry with materialdried (MgSO4)
5. customevaporated under reduced pressure
6. customThe crude product was purified by column chromatography on silica gel

ORD record

ord-2dd2552b21a340acaf7095bdedf5e811

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06251904B1