Water → HCID 13704294, Verbindung

HRID 1583925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583925
[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]=[O:13])=[CH:11][C:5]=2[CH:4]2[O:14][CH:3]12.[NH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[O:21].[H-].[Na+].O>CS(C)=O>[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]=[O:13])=[CH:11][C:5]=2[C@@H:4]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])[C@@H:3]1[OH:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 137042811a,7b-Dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carboxaldehyde

Produkt 1

HCID 13704294HCID 13704294, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 3,4-dihydro-2,2-dimethyl-3,4-epoxy-6-formyl-2H-benzo[b]pyran (0.48 g, prepared using the method described in U.K. Pat. No. 1.511.187) and 2-pyrrolidone (0.20 g) in dry dimethyl sulphoxide (30 ml) was added sodium hydride (0.07 g, 80% dispersion in oil). After stirring at room temperature for 4 hours, water was added and the aqueous phase immediately extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulphate. Filtration, evaporation and chromatography (chromatotron, pentane-ethyl acetate gradient elution, 2 mm silica gel) gave a fraction (150 mgs) which was recrystallised to give the title compound as crystals (80 mgs) of m.p. 196°-197.5° C.

Aufarbeitung

  1. extractionthe aqueous phase immediately extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationFiltration, evaporation and chromatography (chromatotron, pentane-ethyl acetate gradient elution, 2 mm silica gel)
  5. customgave a fraction (150 mgs) which
  6. customwas recrystallised

Quellen und Nachweise

ORD-Eintrag
ord-37f7edebcef94b238815e0a8fe6c891e
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04555509

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