Citric Acid → 3-Benzyloxy-1-isopropyl-4-(4-methoxybenzoyl)-5-phenoxy-1H-pyrazole

HRID 2102263ノート

反応式

HRID 2102263 の反応式
[CH2:1]([O:8][C:9]1[C:13]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:12](Br)[N:11]([CH:25]([CH3:27])[CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C(=O)C>[CH2:1]([O:8][C:9]1[C:13]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:12]([O:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:11]([CH:25]([CH3:27])[CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 230795293-Benzyloxy-5-bromo-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole

生成物 1

HCID 231133743-Benzyloxy-1-isopropyl-4-(4-methoxybenzoyl)-5-phenoxy-1H-pyrazole収率 54.1%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

3-Benzyloxy-5-bromo-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole (43 mg), phenol (14 mg) and potassium carbonate (21 mg) were suspended in N,N-dimethylacetoamide (5 mL) and the mixture was stirred under reflux for 2 hours. The mixture was allowed to cool to room temperature, then 10% citric acid aqueous solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with a saturated sodium hydrogen carbonate and brine. After the solution was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give the title compound, (24 mg).

後処理

  1. temperatureunder reflux for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was sequentially washed with a saturated sodium hydrogen carbonate and brine
  4. dry with materialAfter the solution was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-591d77abe2c24174993ace6b3c9bb3df
出典データセット
uspto-grants-2009_08
特許番号
US07576064B2

反応ノート

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