Methyl iodide → 9H-Xanthen-9-one, 1,5-dimethoxy-3-(2-propenyloxy)-

HRID 585780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585780
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[O:5][C:6]1[CH:7]=[C:8]([O:19][CH2:20][CH:21]=[CH2:22])[CH:9]=[C:10]([OH:18])[C:11]=1[C:12]2=[O:17].[C:23](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C.S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[O:5][C:6]1[CH:7]=[C:8]([O:19][CH2:20][CH:21]=[CH2:22])[CH:9]=[C:10]([O:18][CH3:23])[C:11]=1[C:12]2=[O:17]

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 11403772HCID 11403772, Verbindung

Produkt 1

HCID 121783329H-Xanthen-9-one, 1,5-dimethoxy-3-(2-propenyloxy)-Ausbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1118Sulfuric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of xanthone 2 (150 g, 0.5 mol) in dry DMF (500 mL) was added potassium carbonate (100 g, 0.72 mol) and methyl iodide (180 g, 1.28 mol) and the mixture was heated with constant stirring under argon to 80° C. for 1 hour. The mixture was allowed to cool to room temperature and diluted with 2L ethyl acetate and the remaining potassium carbonate was dissolved in dilute sulfuric acid. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford the xanthone 3 (120 g, 0.38 mol, 77%) as a pale yellow solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto cool to room temperature
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c61f92dbbb224209b02f6fae0cdfaf95
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933396B2

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