1-Octyne → HCID 13588520, compound

Participants

Reaction Conditions

Reaction Steps

Tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol. To a cooled solution (-15° C.) of 1-octyne (7.95 g) in 30 ml of dry tetrahydrofuran under a nitrogen atmosphere was added dropwise 30.4 ml of 2.09M butyllithium in hexane. The addition took 30 minutes, after which the reaction was warmed to 0° C. and then cooled to -10° C. This solution was added slowly to a cold (0° C.) solution of the tetrahydropyranyl ether derivative of hexamethylene bromohydrin (14.80 g) in 50 ml of hexamethylphosphoric triamide under nitrogen. The reaction mixture was allowed to warm to room temperature, stirred overnight, poured into cold water, and extracted three times with hexane. The combined organic layers were washed with water (three times) and brine, and dried with anhydrous Na2SO4. Removal of solvent under reduced pressure yielded 18.55 g of impure tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol as a yellow oil. This material was used without further purification in the next step.

Provenance & Evidence