2,5-dimethyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][-1]benzopyran-7-one → 9-Methoxy-2,5-dimethyl-7h-furo[3,2-g]chromen-7-one

HRID 1448521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448521
[CH3:1][CH:2]1[O:18][C:5]2=[C:6]([O:16][CH3:17])[C:7]3[O:12][C:11](=[O:13])[CH:10]=[C:9]([CH3:14])[C:8]=3[CH:15]=[C:4]2[CH2:3]1>C1(OC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:17][O:16][C:6]1[C:7]2[O:12][C:11](=[O:13])[CH:10]=[C:9]([CH3:14])[C:8]=2[CH:15]=[C:4]2[CH:3]=[C:2]([CH3:1])[O:18][C:5]=12

Komponenten

4

Edukt 1

HCID 203802242,5-dimethyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][-1]benzopyran-7-one

Produkt 1

HCID 1653059-Methoxy-2,5-dimethyl-7h-furo[3,2-g]chromen-7-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

A solution of 10.36 g (0.0422 mol) of 2,5-dimethyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][-1]benzopyran-7-one in 150 ml of diphenyl ether was treated with 6.0 g of 10% palladium on charcoal. The mixture was heated under reflux for 5.0 hrs, cooled, and filtered over celite. The catalyst was further washed with methanol, and the filtrate was then concentrated to remove the methanol. The residue was diluted with 1.5 l. of pet. ether and stirred overnight. The product was filtered, washed with pet. ether, dried, and passed through a silica column, eluting with ethyl acetate/benzene, 1:4, to yield pure 9-methoxy-2,5-dimethyl-7H-furo[3,2-g][1]benzopyran-7-one, m.p. 154°-155° (ethanol).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5.0 hrs
  3. temperaturecooled
  4. filtrationfiltered over celite
  5. washThe catalyst was further washed with methanol
  6. concentrationthe filtrate was then concentrated
  7. customto remove the methanol
  8. additionThe residue was diluted with 1.5 l
  9. filtrationThe product was filtered
  10. washwashed with pet. ether
  11. customdried
  12. washeluting with ethyl acetate/benzene, 1:4

Quellen und Nachweise

ORD-Eintrag
ord-595cbcdb610145bca4b7d088c503e860
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04180659

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