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.

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-7cf65c91a10b435f89a05be088ad0cce

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458951B2