醇发生酯化的反应

案例1：甲磺酰氯

To a solution of the SM (300 mg, 2.30 mmol) in DCM (6 mL) at 0 °C was added TEA (0.64 mL, 4.6 mmol) followed by MeSO₂Cl (0.21 mL, 2.76 mmol). The reaction mixture was stirred at 0 °C for 30 min, then was allowed to warm to RT over 2 h. The mixture was quenched with H2O (10 mL) and extracted with DCM (2 x 20 mL). The combined organics were washed with H2O (20 mL), brine (20 mL), dried (Na2SO4), and concentrated. The resulting material was purified by silica gel column chromatography (35% EtOAc/hexane) to provide the product as a colorless gum. [310 mg, 64%]

Patent Reference: WO2015129926, page 89

案例2：甲磺酸酐

To a solution of the SM (75 mg, 0.24 mmol) in anhydrous DCM (1 mL) was added TEA (0.1 mL, 0.74 mmol). The mixture was cooled in an ice bath and treated with (MeSO₂)₂O (methanesulfonic anhydride) (62 mg, 0.34 mmol). The reaction mixture was removed from the ice bath and stirred for 30 min. The mixture was quenched by the addition of sat aq NaHCO3. The layers were separated and the aq layer was further extracted with DCM (3x). The combined organics were washed with brine, dried (Na2SO4), and concentrated to provide the product as an oil which was taken forward without further purification. [75 mg]

[Patent Reference: WO2012069948, page 53