Pyridine → Cyclopentylmethyl 4-methylbenzene-1-sulfonate

Participants

Reaction Steps

Cyclopentanemethanol p-toluenesulfonate was prepared by the following method: To a solution of cyclopentanemethanol (2.0 g, 20.0 mmol) and pyridine (2.9 ml, 36.3 mmol) in dichloromethane (20 ml) was added p-toluenesulfonyl chloride (3.46 g, 18.1 mmol). The mixture was stirred at room temperature for 24 h under nitrogen. The resulting mixture was washed with 2M hydrochloric acid and the aqueous layer separated and extracted with dichloromethane. The combined organics were dried over sodium sulphate and concentrated under reduced pressure to yield cyclopentanemethanol p-toluenesulfonate as a colourless oil (4.3 g, 17.0 mmol).

Provenance & Evidence