Hydrochloric Acid → HCID 54052927, compound

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.

1. additionAfter addition
2. temperatureThe reaction solution was cooled with ice
3. customThe ether layer was separated
4. extractionthe aqueous layer was extracted twice with ether
5. washthis mixture was washed with a saturated aqueous sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was then removed under reduced pressure
8. customThe residue obtained

ORD record

ord-bd5c794065624edb825b7cd1d05dd4f4

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05004753