Ethanol → Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate

HRID 228619

反応式

HRID 228619 の反応式
[CH:1]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([F:14])=[CH:11][C:12]=2[F:13])=[CH:5][C:4]([C:15]([OH:17])=[O:16])=[C:3]([OH:18])[CH:2]=1.Cl.CN(C)[CH2:22][CH2:23]CN=C=N.O.ON1C2C=CC=CC=2N=N1.C(O)C>CN(C)C=O.O>[F:13][C:12]1[CH:11]=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[C:6]1[CH:5]=[C:4]([C:15]([O:17][CH2:22][CH3:23])=[O:16])[C:3]([OH:18])=[CH:2][CH:1]=1

参加物

7

反応物 4

HCID 702EthanolHCID 3059DiflunisalHCID 27960291-Hydroxybenzotriazole hydrateHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

生成物 1

HCID 23078331Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate収率 67.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Diflunisal (250 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (382 mg), 1-hydroxybenzotriazole hydrate (306 mg), and ethanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 5-(2,4-difluorophenyl)salicylate (188 mg, yield 34%).

後処理

  1. customto prepare a solution which
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-4911f7be4eeb481c95e932840a416975
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

関連ノート

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