Hydrogen Peroxide → 1a,7b-dihydro-2,2-dimethyl-7b-(2-pyridyl)-2H-oxireno[c][1]benzopyran-6-carbonitrile

HRID 1073945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073945
[CH3:1][C:2]1([CH3:20])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:4]=2[O:3]1.C(#N)C.[OH:24]O>CO.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][C:2]1([CH3:20])[CH:7]2[O:24][C:6]2([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:4]=2[O:3]1

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 6342AcetonitrileHCID 156813282,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile

Produkt 1

HCID 198956531a,7b-dihydro-2,2-dimethyl-7b-(2-pyridyl)-2H-oxireno[c][1]benzopyran-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 26052Sodium tungstateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

3 g of 2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carbonitrile and 420 mg of sodium tungstate were heated in 30 ml of methanol and 30 ml of acetonitrile at 50° C. and 12 ml of 30% (w/v) hydrogen peroxide were added. After heating overnight the mixture was evaporated and the residue was taken up in dichloromethane and water. The organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3 and 1:2) for the elution to give 440 mg of 1a,7b-dihydro-2,2-dimethyl-7b-(2-pyridyl)-2H-oxireno[c][1]benzopyran-6-carbonitrile which was used without further purification.

Aufarbeitung

  1. temperatureAfter heating overnight the mixture
  2. customwas evaporated
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-37171f10bbbc4987852fc45877f650f7
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971982

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