3,4-dihydro-2H-pyran → 2-(3-iodopropoxy)tetrahydro-2H-pyran

Participants

Reaction Steps

A solution of 3-iodopropanol (15 g, 80.65 mole), dihydropyran (14.7 ml, 161.29 mole) and pyridium p-toluenesulfonate (500 g, 2.0 mole) in 100 ml of dry dichloromethane was stirred at room temperature under an atmosphere of nitrogen for 2.5 hours. The resulting mixture was diluted with dichloromethane (150 ml), washed with water and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was flash-chromatographed on a silica gel column to give 20.43 g of the title A compound as an oil with a consistent NMR spectrum.

Provenance & Evidence