Water → 1-Octen-3-yl 2,3,3,3-tetrafluoropropionate

In 200 ml of dichloromethane were dissolved 28 g (0.22 mol) of (R)-(-)-1-octen-3-ol (92%ee) and 21 ml (0.26 mol) of pyridine, and then 39.5 g (0.24 mol) of 2,3,3,3-tetrafluoropropionyl chloride was dropwise added to the above-obtained solution while the solution was being cooled with ice. The resulting mixture was stirred at room temperature for 1 hour, subsequently water was added thereto, and then the reaction mixture was subjected to extraction with ether. The resulting extract was washed with 1N hydrochloric acid, a 5% aqueous solution of sodium hydrogencarbonate, and brine, and then dried with magnesium sulfate. Subsequently, the solvent was removed under reduced pressure, and the residual product was distilled at 95° C. under 25 mmHg, thereby obtaining 42.3 g of 1-octen-3-yl 2,3,3,3-tetrafluoropropionate in a yield of 76%.

1. temperaturewas being cooled with ice
2. extractionthe reaction mixture was subjected to extraction with ether
3. extractionThe resulting extract
4. washwas washed with 1N hydrochloric acid
5. dry with materiala 5% aqueous solution of sodium hydrogencarbonate, and brine, and then dried with magnesium sulfate
6. customSubsequently, the solvent was removed under reduced pressure
7. distillationthe residual product was distilled at 95° C. under 25 mmHg

ORD record

ord-575bf172db914618a3549ec067517f6c

Source dataset

uspto-grants-1992_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05126482