To an anhydrous dichloromethane (10 mL) solution of n-butanol (500 mg, 6.7 mmol) was added sequentially pyridine (0.82 mL, 10.1 mmol) and methanesulfonyl chloride (0.78 mL, 10.1 mmol). The reaction mixture was stirred at 0 °C and gradually warmed to room temperature. After 6 hours of reaction, the reaction was quenched with methanol and the reaction solution was subsequently concentrated. The concentrate was diluted with ethyl acetate (50 mL) and washed sequentially with 1 M hydrochloric acid (10 mL), saturated sodium bicarbonate solution (10 mL) and saturated saline (10 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column chromatography to afford n-butyl methanesulfonate (compound 2) as a colorless oil (0.94 g, 92% yield).1H NMR (400 MHz, CDCl3) δ 4.24 (t, J = 13.2, 6.4 Hz, 2H), 3.01 (s, 3H), 1.76-1.72 (m, 2H), 1.48- 1.42 (m, 2H), 0.96 (t, J = 12.8, 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 69.99, 37.30, 31.05, 18.67, 13.48. High-resolution mass spectrometry (ESI) calculated value [C5H12SO3 + Na]+ 175.0405, measured value 175.0401.
