Reaktion #329163

Reaktionsgleichung

magnesium(II) chloride

potassium ethyl malonate

2,6-difluorobenzoic acid

carbonyldiimidazole

hydrochloric acid

→

titled compound

ethyl 3-(2,6-difluorophenyl)-3-oxopropanoate

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwas stirred at 50-60° C. for 6 hours
2. 2
   Temperaturcooled to ambient temperature
3. 3
   workup.ADDITIONwhich was then added via syringe to the solution of activated acid
4. 4
   workup.STIRRINGthe mixture was stirred for an additional 18 hours at ambient temperature
5. 5
   TemperaturThe mixture was refluxed for 3 hours
6. 6
   Temperaturcooled to ambient temperature
7. 7
   ExtraktionThe aqueous layer was extracted with ethyl acetate
8. 8
   Extraktionthe organic extract
9. 9
   Waschenwas washed with water
10. 10
    Trocknendried with sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated in vacuo

Vorschrift

A mixture of 2,6-difluorobenzoic acid (15 g, 0.095 mol) and carbonyldiimidazole (18 g, 0.14 mol, 1.5 equiv) in anhydrous tetrahydrofuran (150 mL) was stirred at ambient temperature for 6 hours. In a separate flask, a suspension of anhydrous magnesium(II) chloride (9.0 g, 0.095 mol, 1.0 equiv) and potassium ethyl malonate (22 g, 0.13 mol, 1.4 equiv) in tetrahydrofuran (225 mL) was stirred at 50-60° C. for 6 hours, cooled to ambient temperature, which was then added via syringe to the solution of activated acid, and the mixture was stirred for an additional 18 hours at ambient temperature. The mixture was refluxed for 3 hours, cooled to ambient temperature, poured into water and acidified with hydrochloric acid (12 N aqueous) to pH<2. The aqueous layer was extracted with ethyl acetate and the organic extract was washed with water, dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

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