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

Participants

Reaction Steps

0.58 ml of 3-bromo-1-propanol was dissolved in 6 ml of dry dichloromethane, and 1.112 ml of dihydropyrane and 10 mg of dry p-toluenesulfonic acid were added thereto. The mixture was stirred at room temperature overnight. The reaction solution was separated with 30 ml. of chloroform and 15 ml of a 4% sodium hydrogencarbonate aqueous solution. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was separated by silica gel column chromatography (chloroform). Then, the fraction containing the product was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1). The combined fraction containing the product was subjected to the removal of the solvent under reduced pressure to obtain 1.44 g of 3-bromo-l-(2-tetrahydropyranyloxy)propane as colorless oily substance.

Provenance & Evidence