Methanol → 2-Methoxy-6-methylpyridine

Sodium (31.0 g, 1.35 mol) was added portionwise to methanol (500 mL) over 30 min with stirring in a flask equipped with a reflux cindenser. After the addition was complete, the reaction mixture was allowed to cool to ambient temperature. 2-Fluoro-6-methylpyridine (50 g, 450 mmol) was added portionwise with stirring. The reaction mixture was then heated to reflux temperature and stirred for 48 h. The mix was then cooled to ambient temperature and solvent was removed in vacuo to provide a yellow oil. The residue was taken up in water (500 mL) and three extractions with ether (200 mL) were performed. The combined organic layers were dried over MgSO4, filtered and solvent was removed in vacuo from the filtrate to give a yellow liquid: 1H-NMR (CDCl3, 300 MHz): δ 7.44 (dd, 1H, J=8, 7), 6.71 (d, 1H, J=7), 6.53 (d, 1H, J=8), 3.91 (s, 3H), 2.45 (s, 3H).

1. customequipped with a reflux cindenser
2. additionAfter the addition
3. stirringwith stirring
4. temperatureThe reaction mixture was then heated
5. temperatureto reflux temperature
6. stirringstirred for 48 h
7. temperatureThe mix was then cooled to ambient temperature
8. customsolvent was removed in vacuo
9. customto provide a yellow oil
10. extractionthree extractions with ether (200 mL)
11. dry with materialThe combined organic layers were dried over MgSO4
12. filtrationfiltered
13. customsolvent was removed in vacuo from the filtrate
14. customto give a yellow liquid

ORD record

ord-7876355e11434604b90960468101999d

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662817B2