p-Toluenesulfonic acid → 2-Butyne, 1,4-bis[(tetrahydropyran-2-yl)oxy]-

Participants

Reaction Conditions

Reaction Steps

104.88 ml (96.69 g, 1.15 mol) of dihydropyran was added dropwise to a solution of 90 g (1.07 mol) of 2-butyn-1,4-diol and 9 g of p-toluenesulfonic acid in 1000 ml of tetrahydrofuran at such a rate to maintain the reaction temperature at 0° C. Thereafter the reaction mixture was stirred for 3 hours at room temperature. It was then neutralized with 10 ml of triethylamine and the solvent removed by evaporation in vacuo. The residue was purified by silica gel column chromatography using hexane:ethyl acetate (80:20) as eluant, to yield 2-butyne-1,4-diol monotetrahydropyranyl ether and 55.33 g (20%) of 2-butyne-1,4-diol bistetrahydropyranyl ether.

Provenance & Evidence