p-Toluenesulfonic acid → (E)-4-methyl-3,5-dioxa-7-decen-9-yne

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Reaction Steps

The 2-trans-penten-4-yn-1-ol (47.7 g) was dissolved in ether (50 ml), cooled to 0° and treated with ethyl vinyl ether (50 mL). To this solution, solid p-toluene sulfonic acid (0.1 g) was added and after a slight exothermic reaction, the mixture was stirred for a further 20 min and quenched with triethylamine (2 mL). The solvents were removed in vacuo and the residue was dissolved in ether, washed with aqueous NaHCO3 solution, dried (MgSO4) and concentrated. The residue was purified by liquid chromatography (two columns, 6:1 parts by volume hexane-ethyl acetate) and distilled, bp 88°-98° (26 mmHg) to give (E)-4-methyl-3,5-dioxa-7-decen-9-yne.

Provenance & Evidence