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

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Reaction Steps

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%.

Provenance & Evidence