Synthesis
Preparation of Example 10-1-1 2-chloromethyl-6-methylpyridine: (6-methylpyridin-2-yl)methanol (1.44 g, 11.7 mmol) was dissolved in dichloromethane (20 mL) and thionyl chloride (1.45 mL, 19.9 mmol) was added. The reaction mixture was stirred under reflux conditions for 40 min. Upon completion of the reaction, the reaction solution was cooled to room temperature and subsequently concentrated under reduced pressure. The concentrated residue was partitioned between sodium bicarbonate solution and ether. The organic layer was separated and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate) to afford the target product 2-chloromethyl-6-methylpyridine (1.42 g, 85.8% yield).1H-NMR (DMSO-d6) δ (ppm): 2.47 (3H, s), 4.72 (2H, s), 7.22 (1H, d, J = 7.6 Hz), 7.33 (1H, d, J = 7.6 Hz), 7.72 (1H, dd, J = 7.6, 7.6 Hz).
References
[1] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10197 - 10204
[2] Patent: US2009/82403, 2009, A1. Location in patent: Page/Page column 64
[3] Patent: US2007/105904, 2007, A1. Location in patent: Page/Page column 61
[4] Chinese Chemical Letters, 2018, vol. 29, # 11, p. 1637 - 1640
[5] Chemistry Letters, 1998, # 9, p. 915 - 916
