Reaction #158354

Reaction equation

3,4,5-trifluorophenol

potassium carbonate

water

ethyl 3-chloro-2-oxopiperidine-3-carboxylate

→

title compound

Yield 79.8%

ethyl 2-oxo-3-(3,4,5-trifluorophenoxy)piperidine-3-carboxylate

Yield 79.8%

Solvents

DMF

brine

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   WashThe extract was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL) and saturated brine (200 mL×2)
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Otherthe solvent was evaporated under reduced pressure
5. 5
   OtherThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Procedure

To a mixture of 3,4,5-trifluorophenol (14.4 g) and potassium carbonate (40.3 g) in DMF (200 mL) was added ethyl 3-chloro-2-oxopiperidine-3-carboxylate (20 g), and the mixture was stirred at 100° C. for 1 hr. To the reaction mixture were added water (200 mL) and saturated brine (200 mL) at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL) and saturated brine (200 mL×2), and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (24.61 g).

Source