p-Toluenesulfonic acid → 1-Bromo-2-(tetrahydropyran-2-yl)oxypropane

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Reaction Steps

5.0 ml of 1-bromo-2-propanol was dissolved in 40 ml of dry dichloromethane, and 7.6 ml of 2,3-dihydropyran and 237 mg of dry p-toluenesulfonic acid were added thereto. The mixture was reacted at room temperature for 5 hours and then diluted by an addition of 250 ml of chloroform. The mixture was washed sequentially with a 4% sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution. Then, the chloroform layer was dried over anhydrous magnesium sulfate. After filtering the inorganic salt off, the filtrate was concentrated under reduced pressure to obtain a brown syrup. This syrup was purified by silica gel flash column chromatography (130 g of Wacogel C-300 and eluted with hexane/ethyl acetate (15/1). The eluate containing the desired product was collected and concentrated under reduced pressure to obtain 11.3 g of 1-bromo-2-(tetrahydropyran-2-yl)oxypropane as a colorless transparent volatile syrup.

Provenance & Evidence