Triethylamine → HCID 18760350, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 15 g (0.088 mol) of the foregoing monotetrahydropyranyl ether and 19.79 ml (14.25 g, 0.141 mol) of triethylamine in 250 ml of anhydrous methylene chloride, there were added dropwise 10.24 ml (15.15 g, 0.1323 mol) of methanesulfonyl chloride, at such a rate to maintain the reaction temperature at 0° C., stirring the reaction mixture for 30 minute further at 0° C. It was then poured into aqueous saturated sodium bicarbonate solution and extracted with methylene chloride. The combined organic extracts were dried and evaporated, to yield 4-tetrahydropyranyloxybut-2-yn-1-ol methanesulfonate, in almost quantitative yield. This crude product was dissolved in 50 ml of acetone and treated with a solution of 40.34 g (0.4636 mol) of lithium bromide in 200 ml of acetone, stirring the reaction mixture at room temperature for 1 hour. The solvent was then evaporated and the residue diluted with water and extracted with methylene chloride, the organic extracts were dried and evaporated in vacuo. The crude material was purified by silica gel column chromatography using hexane-ethyl acetate (95:5) as eluant, to yield 1-bromobut-2-yn-4-ol-tetrahydropyranyl ether, as an oil.

Provenance & Evidence