Hydrogen Peroxide → 2,3-Epoxychromone

HRID 1940007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940007
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[OH:12]O>CCOCC>[O:12]1[C:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[O:1][C:2]1=2

Komponenten

4

Edukt 2

HCID 784Hydrogen PeroxideHCID 10286Chromone

Produkt 1

HCID 214655662,3-EpoxychromoneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Chromone (3 g) was dissolved in ether (200 ml) and the solution was cooled to 0° C. in ice water. Then, 30% hydrogen peroxide (15 ml) and Triton B (10 ml) solution were added portionwise. The whole was stirred at 0° C. for 4 hours. After adding ice water, the reaction liquor was extracted with dichloromethane. The organic layer was washed with sodium thiosulfate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was fractionatedby silica gel column chromatography (diethyl ether/hexane =1:8) to give the titled compound (2.34 g; yield =75%). Melting point: 66°-67° C. Mass spectrum (M+): 162. 1H-NMR(CDCl3, δ ppm): 3.69 (d, 1H, H3), 5.67 (d, 1H, H2), 7.05 (d, 1H, H8), 7.14 (t, 1H, H6), 7.54 (t, 1H, H7), 7.79 (dd, 1H, H5).

Aufarbeitung

  1. extractionthe reaction liquor was extracted with dichloromethane
  2. washThe organic layer was washed with sodium thiosulfate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-356d6a7794d84949845b5a6a9c170b34
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698575

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