Water → 5-Ethoxymethoxy-benzofuran

HRID 217206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217206
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH2:13]([O:15][CH2:16]Cl)[CH3:14].O>CN(C=O)C>[CH2:13]([O:15][CH2:16][O:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[CH:3][C:4]=2[CH:9]=1)[CH3:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 11651159Benzofuran-5-ol

Produkt 1

HCID 592274505-Ethoxymethoxy-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of benzofuran-5-ol (2) (257 mg, 1.92 mmol) in DMF (3 mL), NaH (81 mg, 1.92 mmol, 57% dispersion in oil) was added at 0° C. The reaction mixture was warmed to room temperature and stirred 1 hour. Chloromethyl ethyl ether (214 μL, 2.30 mmol) was then added drop wise to 0° C. and the mixture was stirred at room temperature for additional 1 hour. Water (10 mL) was added and the reaction mixture was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with water, brine, dried over Na2SO4, and concentrated in vacuo. Purification of the crude product by flash column chromatography using 10% ethyl acetate in hexane afforded compound (3) (273 mg) as a colourless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for additional 1 hour
  2. extractionthe reaction mixture was extracted with ethyl acetate (2×50 mL)
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude product by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bcd7bfa677e64f72a143dd07740c793d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193363B2

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