Hydrochloric Acid → Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate

HRID 500523노트

반응식

HRID 500523 반응식
[H-].[Na+].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:5].[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[O:19])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:5])[CH3:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 149331-(3-Chlorophenyl)ethanoneHCID 24758Sodium hydride

생성물 1

HCID 11054223Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate수율 67%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (60% oil dispersion, 1.24 g, 31.1 mmol) was added in portions to a solution of 3-chloroacetophenone (4.0 g, 26 mmol) and diethyl oxalate (4.54 g, 31.1 mmol) in DMF (32 mL) at 0° C. The mixture stirred at room temperature for 1 hour and was then heated at 80° C. for a half an hour. After cooling, the mixture was treated with 3 M HCl and then diluted with ethyl acetate. The organic layer was washed with water (three times) and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was then purified by flash column chromatography on silica using 0-10% ethyl acetate in hexanes to afford of the title compound (4.43 g, 67%, yellow solid).

후처리

  1. temperaturewas then heated at 80° C. for a half an hour
  2. temperatureAfter cooling
  3. washThe organic layer was washed with water (three times) and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was then purified by flash column chromatography on silica using 0-10% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-98272adf4af84d2286acf2a53377f06d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772235B2

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