Synthesis
Hexanol (50 mmol, 1 eq.) and triethylamine (11.08 mL, 80 mmol, 1.6 eq.) were dissolved in dichloromethane (60 mL), and the reaction system was cooled to 0 °C. Subsequently, methanesulfonyl chloride (4.33 mL, 56 mmol, 1.12 eq.) was slowly added dropwise via syringe. The reaction mixture was stirred at 0 °C for 30 min, then brought to room temperature and continued to stir overnight. After completion of the reaction, the organic layer was washed sequentially with 1 M hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Finally, hexyl methanesulfonate was purified by silica gel column chromatography (eluent ratio: ethyl acetate:petroleum ether=1:2).
References
[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7753 - 7759
[2] Journal of the American Chemical Society, 1985, vol. 107, # 18, p. 5210 - 5219
[3] Journal of Fluorine Chemistry, 2018, vol. 214, p. 35 - 41
[4] Journal of the Electrochemical Society, 2010, vol. 157, # 9, p. F124-F129
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 35, p. 4850 - 4856
