Propargyl alcohol → HCID 21507774, compound

Participants

Reaction Steps

460 ml of a solution of ethyl magnesium bromide in tetrahydrofuran titrating 0.71 moles per liter were added dropwise to a solution of 9 g of propargyl alcohol in 100 ml of tetrahydrofuran and after stirring the mixture for 11/2 hours, a solution of 35.6 g of α-chloro-heptanal in 100 ml of tetrahydrofuran was added thereto. The mixture was stirred for one hour and was then poured into a saturated aqueous monosodium phosphate solution. The mixture was extracted with ether and the organic phase was washed with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure at 100°C. The residue was chromatographed over silica gel and was eluted with a 4-1 benzene-ethyl acetate mixture to obtain 16.6 g of 5-chloro-4-hydroxy-2-decynol in the form of a yellow oil.

Provenance & Evidence