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2-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-one → Eupatilin

HRID 377351
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HRID 377351 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[O:9]2)=[C:4]([O:23]C)[C:3]=1[O:25][CH3:26].[Cl-].[Cl-].[Cl-].[Al+3]>C(#N)C>[OH:23][C:4]1[C:3]([O:25][CH3:26])=[C:2]([OH:1])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:22])[CH:7]=[C:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[O:9]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 54916432-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-oneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 5273755Eupatilin수율 74.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

After 7-hydroxy-3',4',5,6-tetramethoxy flavone (4.44 g, 12.4 mmol) was suspended in 88 mL of acetonitrile and aluminum trichloride (8.27 g, 5 equivalents) was added hereto at room temperature, the reaction mixture was refluxed for 1.5 hour and the solvent was removed by evaporation under reduced pressure. To the residue was added 10% aqueous solution of hydrochloric acid and chloroform, then the solution was refluxed until it became clear. After the solution was cooled to room temperature, the organic layer was washed with water and brine, then dried over anhydrous magnesium sulfate and the solvent of the organic layer was removed by reduced pressure. The residue was recrystallized in methanol to afford 3.18 g of the product (74%).

후처리

  1. temperaturethe reaction mixture was refluxed for 1.5 hour
  2. customthe solvent was removed by evaporation under reduced pressure
  3. additionTo the residue was added 10% aqueous solution of hydrochloric acid and chloroform
  4. temperaturethe solution was refluxed until it
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent of the organic layer was removed by reduced pressure
  8. customThe residue was recrystallized in methanol

출처 및 근거

ORD 기록
ord-b2db93f7b6184ac6a5729904546705ce
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06025387

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