Synthesis
General procedure for the synthesis of (4-methyl-pyridin-2-yl)-methanol from 2,4-dimethylpyridine 1-oxide: to a solution of 2,4-dimethylpyridine 1-oxide (10.11 g, 82.10 mmol) in dichloromethane (DCM, 200 mL) was added slowly and dropwise Trifluoroacetic acid anhydride (TFAH, 51.37 g, 244.6 mmol) in a dichloromethane (DCM, 50 mL) solution. The reaction mixture was stirred at room temperature for 3.5 days. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. Methanol (MeOH, 200 mL) and saturated potassium carbonate (K2CO3, 250 mL) solution was then added and the mixture continued to be stirred for 3 hours at room temperature. Methanol was again removed by concentration under reduced pressure and the residue was extracted with dichloromethane (200 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give 4 g of a brown oily product in 39.6% yield.
References
[1] Patent: CN106749268, 2017, A. Location in patent: Paragraph 0833; 0834
[2] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[3] Pharmaceutical Bulletin, 1955, vol. 3, p. 413,415
[4] Yakugaku Zasshi, 1956, vol. 76, p. 900
[5] Chem.Abstr., 1957, p. 2770
