4-Toluenesulfonyl chloride → 3-Methoxypropyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of 3-methoxypropan-1-ol (15.9 mL, 166 mmol) in CH2Cl2 (75 mL) and pyridine (50 mL) was added DMAP (1.0 g, 8.32 mmol), followed by p-toluenesulfonyl chloride (31.7 g, 166 mmol). This mixture was allowed to stir at ambient temperature for 72 hours, then was quenched with 5% aqueous HCl (30 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 (31 g, 127 mmol, 76% yield). MS (DCI/NH3) m/z 262 (M+NH4).

Provenance & Evidence