Water → HCID 178441857, Verbindung

HRID 486019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486019
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH2:16][OH:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C)C=O>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:16]=[O:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 178441858HCID 178441858, Verbindung

Produkt 1

HCID 178441857HCID 178441857, VerbindungAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.3 g of 2-butyl-6-(hydroxymethyl)-4(1H)-quinazolinone in 3.5 ml of dry N,N-dimethylformamide is added 1.7 g of pyridinium dichromate. The reaction mixture is stirred at room temperature for 16 hours and then poured into 125 ml of water. The resulting precipitate is removed by filtration and the filtrate extracted with 9:1 chloroform-methanol. The combined organic extracts are dried over magnesium sulfate, filtered and concentrated in vacuo and combined with the precipitate above. The combined solids are purified by flash chromatography on silica gel by eluting with 1:1 ethyl acetate-hexanes to give 0.27 g of the desired product. CI MASS SPEC 231(M+H).

Aufarbeitung

  1. customThe resulting precipitate is removed by filtration
  2. extractionthe filtrate extracted with 9:1 chloroform-methanol
  3. dry with materialThe combined organic extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe combined solids are purified by flash chromatography on silica gel
  7. washby eluting with 1:1 ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5384cabd8e984d589c8ae2e30345e80f
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290780

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