Water → Methyl {6-[(4-ethoxybenzyl)oxy]-1-benzofuran-3-yl}acetate

HRID 1888706

Reaktionsgleichung

Reaktionsgleichung von HRID 1888706
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.Cl[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][O:1][C:2]2[CH:15]=[CH:14][C:5]3[C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][O:8][C:4]=3[CH:3]=2)=[CH:19][CH:20]=1)[CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20639711-(Chloromethyl)-4-EthoxybenzeneHCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Produkt 1

HCID 58047549Methyl {6-[(4-ethoxybenzyl)oxy]-1-benzofuran-3-yl}acetateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl (6-hydroxy-1-benzofuran-3-yl)acetate (10.0 g, 48.5 mmol) in DMF (100 mL) were added 1-(chloromethyl)-4-ethoxybenzene (12.4 g, 72.7 mmol) and potassium carbonate (13.5 g, 97.0 mmol), and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with diethyl ether and hexane to give the title compound (15.8 g, yield 96%) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed twice with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was washed with diethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-4265bbe240764c999ee95da68580826f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501804B2

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