Hydrochloric Acid → (Z)-3-hydroxy-4-fluoro-4-hepten-1-yne

After 13.0 g of (Z)-2-fluoro-2-pentenal was dissolved in 30 ml of dry tetrahydrofurane, a tetrahydrofurane solution of acetylene magnesium bromide (the molar amount of acetylene magnesium bromide was 1.5 times that of the said aldehyde) was added to the solution dropwise while it was cooled with ice and maintained at a temperature of 10° C. or below. The mixture was stirred for 30 minutes while being cooled with ice and then stirred at 20° C. for one hour. The reaction solution was poured into ice-cooled 5% dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was distilled under reduced pressure, thereby obtaining 9.5 g of the desired substance as a pale yellow oil.

1. additionwas added to the solution dropwise while it
2. temperaturewas cooled with ice
3. temperaturemaintained at a temperature of 10° C. or below
4. temperaturewhile being cooled with ice
5. stirringstirred at 20° C. for one hour
6. additionThe reaction solution was poured into ice-
7. extractionextracted with ethyl acetate
8. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous magnesium sulfate
10. distillationAfter the solvent was distilled off
11. distillationthe residue was distilled under reduced pressure
12. customobtaining 9.5 g of the desired substance as a pale yellow oil

ORD record

ord-89a1c75b0b3f48e2ac35a2ea21e5d04f

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04774369