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

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Reaction Steps

3-Butyn-1-ol (3) (7.0 g, 100 mmol) was dissolved in 50 mL dry ether, and the solution was cooled to 0°. A few crystals of p-toluenesulphonic acid were added, followed by dropwise addition of 9.24 g (110 mmol) of dihydropyran. The resulting solution was warmed to 20°, stirred for 16 hr, and extracted with saturated aqueous NaHCO3 (20 mL) and brine (20 mL). The solution was dried (MgSO4), concentrated in vacuo, and distilled to give 7 (14.78 g, 96% yield).

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