1-Pentanol → Pentyl toluene-4-sulphonate

Participants

Reaction Steps

To a solution of pentan-1-ol (9.2 mL, 85 mmol) in CH2Cl2 (70 mL) and pyridine (50 mL) was added DMAP (0.52 g, 4.3 mmol) followed by p-toluenesulfonyl chloride (16.2 g, 85 mmol). This mixture was allowed to stir at ambient temperature for 18 hours then quenched with 5% aqueous HCl (20 mL) and diluted with EtOAc (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×7 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 75% hexanes in EtOAc) to give the title compound (13.1 g, 53.9 mmol, 63% yield). MS (DCI/NH3) m/z 260 (M+NH4)−.

Provenance & Evidence