Potassium Carbonate → 1-{5-[(4-Ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanone

HRID 1888741

Reaktionsgleichung

Reaktionsgleichung von HRID 1888741
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=2[CH:13]=1.[CH2:14]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH2:14]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=3[CH:13]=2)=[CH:19][CH:18]=1)[CH3:15]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 20639711-(Chloromethyl)-4-EthoxybenzeneHCID 32378771-(5-Hydroxy-1-benzofuran-2-yl)ethanone

Produkt 1

HCID 670158661-{5-[(4-Ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanoneAusbeute 163,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 1-(5-hydroxy-1-benzofuran-2-yl)ethanone (2.40 g, 13.7 mmol) in anhydrous DMF (1 mL) were added 4-ethoxybenzyl chloride (2.81 g, 16.5 mmol) and potassium carbonate (3.78 g, 27.4 mmol) and the mixture was stirred at 50° C. overnight. Saturated brine was added thereto, and the mixture was extracted three times with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1-{5-[(4-ethoxybenzyl)oxy]-1-benzofuran-2-yl}ethanone (6.95 g). This was directly used for the next reaction.

Aufarbeitung

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-852283389d0e4a479baaeb76ed08dc28
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501804B2

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