Sulfuric Acid → Isoxanthohumol

HRID 564214

Reaktionsgleichung

Reaktionsgleichung von HRID 564214
C=CCO[C@H](C1C2C(=CC=CC=2)N=CC=1)[C@H]1[N+]2(CC3C4C(=CC=CC=4)C=C4C=3C=CC=C4)C[C@H](C=C)[C@@H](CC2)C1.[Br-].[CH3:42][C:43]([CH3:67])=[CH:44][CH2:45][C:46]1[C:47]([OH:66])=[CH:48][C:49]([O:64][CH3:65])=[C:50]([C:53](/[CH:55]=[CH:56]/[C:57]2[CH:58]=[CH:59][C:60]([OH:63])=[CH:61][CH:62]=2)=[O:54])[C:51]=1[OH:52].[OH-].[Na+].OS(O)(=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:42][C:43]([CH3:67])=[CH:44][CH2:45][C:46]1[C:47]([OH:66])=[CH:48][C:49]([O:64][CH3:65])=[C:50]2[C:53](=[O:54])[CH2:55][CH:56]([C:57]3[CH:58]=[CH:59][C:60]([OH:63])=[CH:61][CH:62]=3)[O:52][C:51]=12

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 639665XanthohumolHCID 10886583O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide

Produkt 1

HCID 513197Isoxanthohumol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To the suspension of the O'Donnell phase transfer catalyst O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (34 mg, 0.056 mmol) in 1 ml of toluene is added xanthohumol (2 OH groups protected) (in part TIPS-protected: 37 mg, 0.056 mmol) in 1 ml of toluene. Subsequently, 0.5 ml of 25% NaOH is added and the mixture is stirred for 24 h at room temperature. For workup, 20 ml of H2O and 20 ml of ethyl acetate are added. The aqueous phase is acidified with H2SO4 and extracted twice with ethyl acetate. The organic phase is washed with NH4Cl solution and H2O, dried and eluted through a silica gel column using CHCl3/methanol. Removal of protection proceeds in a manner known from the literature.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phase is washed with NH4Cl solution and H2O
  3. customdried
  4. washeluted through a silica gel column
  5. customRemoval of protection proceeds in a manner

Quellen und Nachweise

ORD-Eintrag
ord-8414655f00644a008ccf2d4329be30ca
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067622B2

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