Synthesis
A solution of methyl 2-methylnicotinate (35.2 g, 234 mmol) in 275 ml of dry ether was added dropwise to a vigorously stirred suspension of LiAlH4 (13.3 g, 350 mmol) in 600 ml of anhydrous ether. The reaction mixture was heated and refluxed in an oil bath at 55°C for 1.5 h and subsequently cooled to 0°C. H2O (64 ml) was added slowly dropwise, and the reaction was carried out for 1 h. The supernatant was decanted. The remaining suspension was extracted with ether. All organic phases were combined, dried over MgSO4 and the solvent was evaporated to give 29.9 g (234 mmol, 100% yield) of 3-(hydroxymethyl)-2-methylpyridine, the product being an orange-colored oil; GC analysis showed 100% purity.
References
[1] Patent: US2002/49316, 2002, A1
[2] Patent: US2005/124586, 2005, A1. Location in patent: Page/Page column 9-10
[3] Patent: WO2009/147211, 2009, A1. Location in patent: Page/Page column 25
[4] Patent: WO2009/42694, 2009, A1. Location in patent: Page/Page column 75
[5] Patent: US2004/6114, 2004, A1. Location in patent: Page 71
