4-Toluenesulfonyl chloride → Cyclobutylmethyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of cyclobutanemethanol (11.0 mL, 116 mmol) in CH2Cl2 (35 mL) and pyridine (35 mL) was added DMAP (0.71 g, 5.81 mmol) followed by p-toluenesulfonyl chloride (22.1 g, 116 mmol). This mixture was allowed to stir at ambient temperature for 16 hours then was quenched with 5% aqueous HCl (40 mL) and diluted with CH2Cl2 (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, eluted with 75% hexanes in EtOAc) to give the title compound (24.7 g, 103 mmol, 89% yield). MS (DCI/NH3) m/z 258 (M+NH4)+.

Provenance & Evidence