Flavokavain A → 1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-1-propanone

HRID 1030727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030727
[OH:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:3]=1[C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:3]=1[C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

Komponenten

5

Edukt 2

HCID 235736Flavokavain AHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 2700571-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-1-propanoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Then, 100 ml of an ethyl acetate solution of 10.0 g of 2'-hydroxy-4,4',6'-trimethoxychalcone was added to a suspension of 2.0 g of 5% palladium/carbon in 50 ml of ethyl acetate, in which a hydrogen gas had been sufficiently absorbed in advance, and the mixture was stirred at room temperature for 1 hour in a hydrogen gas atmosphere. After the reaction, the reaction mixture was filtered and the solvent was removed from the filtrate by distillation, and the obtained residue was recrystallized from a mixed solvent of methanol and ethyl acetate to obtain 9.3 g (yield=93.0%) of 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-1propanone in the form of a colorless needle.

Aufarbeitung

  1. customhad been sufficiently absorbed in advance
  2. customAfter the reaction
  3. filtrationthe reaction mixture was filtered
  4. customthe solvent was removed from the filtrate by distillation
  5. customthe obtained residue was recrystallized from a mixed solvent of methanol and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-59eb0f2e0c8748a8923496a43d62662d
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106871

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