Hydrochloric Acid → Ethyl 3-(2,6-difluorophenyl)-3-oxopropanoate

HRID 241981

반응식

HRID 241981 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl-].[Mg+2].[Cl-].[C:27]([O:33][CH2:34][CH3:35])(=[O:32])[CH2:28]C([O-])=O.[K+].Cl>O1CCCC1.O>[F:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[C:3]=1[C:4](=[O:6])[CH2:28][C:27]([O:33][CH2:34][CH3:35])=[O:32]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 97962,6-Difluorobenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

생성물 1

HCID 13550002Ethyl 3-(2,6-difluorophenyl)-3-oxopropanoate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  1. stirringwas stirred at 50-60° C. for 6 hours
  2. temperaturecooled to ambient temperature
  3. additionwhich was then added via syringe to the solution of activated acid
  4. stirringthe mixture was stirred for an additional 18 hours at ambient temperature
  5. temperatureThe mixture was refluxed for 3 hours
  6. temperaturecooled to ambient temperature
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. extractionthe organic extract
  9. washwas washed with water
  10. dry with materialdried with sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-aa0c7c90c9db4181bb4de98653e3f5ed
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653079B2

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