p-Toluenesulfonic acid → 2-[(Hept-6-yn-2-yl)oxy]oxane

Participants

Reaction Steps

Alcohol 5 (7.7 g, 68.75 mmol) was dissolved in 75 mL dry ether and cooled to 0°. A few crystals of p-toluenesulphonic acid were added, followed by dropwise addition of 6.35 g (75.6 mmol) of dihydropyran. The solution was warmed to 20°, stirred for 18 hr, and then extracted with saturated aqueous NaHCO3 (25 mL) and brine (25 mL). The solution was dried (MgSO4), concentrated in vacuo, and distilled, yielding 12.96 g of 6 (96% yield).

Provenance & Evidence