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Isopropanol → 4-[2-(3,5-Dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylic acid

HRID 1937422
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HRID 1937422 반응식
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][CH:9]([C:11]1[C:16]2[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[O:19][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)[OH:10].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[Cl:27][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]([C:11]1[C:16]2[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[O:19][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10]
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참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 22734474Ethyl 4-[2-(3,5-dichloro-4-pyridyl)-1-hydroxyethyl]-7-methoxybenzofuran-2-carboxylateHCID 131709961Jones' reagent

생성물 1

HCID 227341684-[2-(3,5-Dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylic acid수율 90%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Ethyl 4-[2-(3,5-dichloro-4-pyridyl)-1-hydroxyethyl]-7-methoxybenzofuran-2-carboxylate (10 g) was dissolved in acetone (200 ml), a Jones reagent (a 2.76 mmol/L solution, 9.7 ml) was dropwise added thereto under cooling on ice, and the mixture was stirred for 20 minutes. Isopropanol was added thereto, and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure and the residue was extracted with chloroform. The extract was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was suspended in isopropanol and the precipitated crystals were collected by filtration to give the desired compound (8.34 g, 84%) as colorless crystals.

후처리

  1. temperatureunder cooling on ice
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washThe extract was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. filtrationthe precipitated crystals were collected by filtration

출처 및 근거

ORD 기록
ord-6168e4becc274801aa34bdddb7827e6c
출처 데이터셋
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06395738B1

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