General procedure for the synthesis of 6-methyl-3-(1-hydroxyethyl)pyridine from 1-(6-methylpyridin-3-yl)ethanone: Sodium borohydride (2.3 g, 0.06 mol) was added in batches to a solution of 1-(6-methylpyridin-3-yl)ethanol (160 ml) of 1-(6-methylpyridin-3-yl)ethanone (16.4 g, 0.121 mol) at 30 °C, maintaining a constant temperature and continuously stirring the reaction mixture. After 1 hour of reaction, the reaction mixture was diluted with saturated sodium bicarbonate solution (2 x 200 ml) and subsequently extracted with dichloromethane (2 x 500 ml). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give a light yellow oil. The crude product was purified by fast column chromatography (eluent: 5% methanol/dichloromethane) to afford 6-methyl-3-(1-hydroxyethyl)pyridine (17.0 g, two-step yield 93%) as a pale yellow oil.ES-MS [M + 1]+ : 138.1. 1H NMR (400 MHz, CDCl3): δ 8.35 (d, J = 2.0 Hz, 1H), δ 7.63 (dd, J = 8.0,2.4 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 4.89 (q, J = 6.5 Hz, 1H), 3.30 (brs, 1H), 2.50 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H).
