Hydrochloric Acid → HCID 54052927, compound

Participants

Reaction Steps

2.35 Grams of (Z)-6-chloro-2-fluoro-2-hexenal was dissolved in 20 ml of dry tetrahydrofuran, and to the resulting solution was added dropwise a tetrahydrofuran solution of ethynylmagnesium bromide (1.5 equivalents vs. the aldehyde) with ice-cooling. After addition, the solution was stirred at room temperature for 10 hours. The reaction solution was cooled with ice, and after adding 50 ml of ether, poured into 10% hydrochloric acid. The ether layer was separated, and the aqueous layer was extracted twice with ether. The ether extracts were combined with the above ether layer, and this mixture was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was then removed under reduced pressure. The residue obtained was treated by column chromatography on silica gel with an ethyl acetate/hexane (1:5) mixture as an eluent to obtain 1.72 g of 8-chloro-4-fluoro-3-hydroxy-4-octen-1-yne as a pale yellow oily product.

Provenance & Evidence