In 200 mL of dichloromethane, tetrahydro-2H-pyran-4-ol (15.83 g, 0.155 mol) was mixed with triethylamine (21.6 mL, 0.155 mol) and dimethylaminopyridine (1.89 g, 0.015 mol) was added as a catalyst. Methanesulfonyl chloride (12 mL, 0.155 mol) was slowly added dropwise at 0 °C. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirred continuously for 16 hours. After completion of the reaction, the organic phase was washed sequentially with deionized water and brine, and then dried with anhydrous magnesium sulfate. After filtration to remove the drying agent, the solvent was removed by distillation under reduced pressure to afford tetrahydro-2H-pyran-4-yl methanesulfonate (Compound 1010, 22.6 g, 80.9% yield) as a yellow solid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.90 (qn, J = 4.2 Hz, 1H), 3.95 (dt, J = 12.0, 4.2 Hz, 2H), 3.59-3.51 (m, 2H), 3.04 (s, 3H), 2.08-2.01 (m, 2H), 1.94-1.82 (m, 2H).
