p-Toluenesulfonic acid → 2-(3-Bromopropoxy)tetrahydro-2H-pyran

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Reaction Steps

0.58 ml of 3-bromo-1-propanol was dissolved in 6 ml of dry dichloromethane, and 1.22 ml of dihydropyran and 10 mg of dry p-toluenesulfonic acid were added thereto. The mixture was stirred at room temperature overnight, and the mixture was partitioned with 30 ml of chloroform and 15 ml of a 4% sodium hydrogencarbonate aqueous solution. The organic solvent layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was separated by silica gel column chromatography (10 g of Kieselgel 60) by using chloroform. Then, the fraction containing the product was purified by silica gel column chromatography (10 g of Kieselgel 60) by using a mixture of n-hexane/ethyl acetate (20/1). The fractions containing the product were put together, and the solvent was distilled off under reduced pressure to obtain 1.44 g of 3-bromo-1-(2-tetrahydropyranyloxy)propane as a colorless oily substance.

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