Triethylamine → (S)-(+)-2-fluoro-2-(trifluoromethyl)-4-hexenoic acid

In 1 ml of dichloromethane was dissolved 0.18 g of 3-buten-2-yl 2,3,3,3-tetrafluoropropionate as obtained in Reference Example 1, and the resulting solution was cooled with ice under a nitrogen atmosphere. Thereto were added 0.29 g of trimethylsilyl triflate and 0.21 g of triethylamine, and the resulting mixture was stirred at room temperature for 36 hours. Then, the reaction mixture was poured into a 5% aqueous solution of potassium carbonate, and the aqueous layer was washed with ether. The resulting aqueous layer was acidified with concentrated hydrochloric acid, and then extracted with dichloromethane. The resulting extract was dried with magnesium sulfate, and the solvent was removed under reduced pressure. Subsequently, the residual product was distilled to obtain 0.14 g of (S)-(+)-2-fluoro-2-(trifluoromethyl)-4-hexenoic acid having the physical properties as mentioned hereinbefore.

1. customas obtained in Reference Example 1
2. temperaturethe resulting solution was cooled with ice under a nitrogen atmosphere
3. washthe aqueous layer was washed with ether
4. extractionextracted with dichloromethane
5. extractionThe resulting extract
6. dry with materialwas dried with magnesium sulfate
7. customthe solvent was removed under reduced pressure
8. distillationSubsequently, the residual product was distilled

ORD record

ord-db0d4053221d4089860f8f98408e9484

Source dataset

uspto-grants-1992_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05126482