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

HRID 1937422
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1937422
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6168e4becc274801aa34bdddb7827e6c
Quelldatensatz
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06395738B1

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