Pyridine → 1-Chloroethyl Hexyl Carbonate

A mixture solution of 3.130 g of n-hexanol [Compound (10)] and 2.42 g of pyridine in 30 ml of dry dichloromethane was cooled to -78° C. To this mixture solution was added dropwise a solution of 4.289 g of 1-chloroethylchloroformate in 15 ml of dry dichloromethane for 1 hour. Then, the reaction mixture was stirred for 1.5 hour under ice-cooling and for 15 hours at room temperature. After the reaction, ethyl acetate was added to the reaction mixture. The organic layer was washed with 1N--HCl, saturated sodium bicarbonate aqueous solution and saturated saline solution respectively, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane: chloroform=3:1) to give 5.697 g (91%) of 1-(n-hexyloxycarbonyloxy)ethyl-chloride [Compound (11)].