Pyridine → 1-(2-p-Toluenesulphonyloxyethyl)cyclopropanol

Participants

Reaction Steps

To an ice-cooled solution of 1-(2-hydroxyethyl)cyclopropanol (1.31 g) and pyridine (4 ml) in dichloromethane (20 ml) was added p-toluenesulphonyl chloride (4.7 g). The mixture was then stirred at room temperature under an atmosphere of nitrogen for 5 hours before being partitioned between ether (100 ml) and water. The organic layer was washed consecutively with 1N hydrochloric acid, water, 5% sodium hydrogen carbonate solution, and brine, and dried. Concentration in vacuo gave a residue which was purified by chromatography (150 g silica gel; 40% ethyl acetate in petroleum ether as eluant) to give the 1-(2-p-toluenesulphonyloxyethyl)cyclopropanol [E; n=1, R1 +R2 =--(CH2)2 --] as an oil.

Provenance & Evidence