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

HRID 241981

反応式

HRID 241981 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aa0c7c90c9db4181bb4de98653e3f5ed
出典データセット
uspto-grants-2014_02
特許番号
US08653079B2

関連ノート

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