Propargyl alcohol → HCID 21507774, compound

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.

1. stirringThe mixture was stirred for one hour
2. extractionThe mixture was extracted with ether
3. washthe organic phase was washed with water
4. dry with materialdried over magnesium sulfate
5. customevaporated to dryness under reduced pressure at 100°C
6. customThe residue was chromatographed over silica gel
7. washwas eluted with a 4-1 benzene-ethyl acetate mixture

ORD record

ord-df62193fe50c48c3abd803b0a6a1ab47

Source dataset

uspto-grants-1976_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03984442