Synthesis
1) A mixture of 2-hydroxy-6-methylpyridine (164 g, 1.47 mol), iodomethane (1.35 kg, 9.53 mol) and Ag2CO3 (526 g, 1.91 mol) in THF (10 mL) was stirred at ambient temperature for 1 hr under light-avoiding conditions.2) Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the mixture was washed with THF The filter cake was washed with THF. 3) The filtrates were combined and concentrated in vacuum until complete removal of methyl iodide was confirmed by HPLC analysis to give 145.6 g of 2-methoxy-6-methylpyridine in 80% yield.
References
[1] Tetrahedron Letters, 1997, vol. 38, # 35, p. 6153 - 6156
[2] Synthetic Communications, 1994, vol. 24, # 10, p. 1367 - 1379
[3] Tetrahedron, 2000, vol. 56, # 20, p. 3181 - 3187
[4] Patent: US2006/287292, 2006, A1. Location in patent: Page/Page column 28
[5] Patent: US2007/281918, 2007, A1. Location in patent: Page/Page column 13
