General procedure for the synthesis of 6-methyl-3-methanolpyridine from 6-methylnicotinic acid methyl ester: To a stirred solution of 6-methylnicotinic acid methyl ester (21 g; 140 mmol; 1 eq.) in anhydrous THF (150 mL) was added slowly and dropwise to a THF solution (210 mL; 210 mmol; 1.5 eq.) of 1 M LiAlH4 at -5 °C. After the dropwise addition, the reaction mixture was continued to be stirred at 23 °C for 2 hours. Subsequently, the mixture was cooled to -10 °C and the reaction was carefully quenched with sodium sulfate decahydrate and ethyl acetate until bubbling ceased. The mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated to dryness under reduced pressure to afford 6-methyl-3-methanolpyridine (17 g, 100% yield). The product was characterized by 1H NMR (DMSO-d6): δ 8.37 (s, 1H), 7.59 (dd, 1H, J = 2,8Hz), 7.19 (d, 1H, J = 8Hz), 5.22 (t, 1H, J = 6Hz), 4.47 (d, 2H, J = 6Hz), 2.45 (s, 3H).
