Sodium Hydroxide → HCID 54187119, Verbindung

HRID 223128

Reaktionsgleichung

Reaktionsgleichung von HRID 223128
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]2[O:7][C:8]3[C:13]([C:14](=[O:18])[C:15]=2[O:16][CH3:17])=[C:12]([OH:19])[CH:11]=[C:10]([O:20][CH3:21])[CH:9]=3)=[CH:4][C:3]=1[O:24][CH3:25].C([O:29][C@@H:30]1[C@@H:35]([O:36]C(=O)C)[C@H:34]([O:40]C(=O)C)[C@@H:33]([CH2:44][O:45]C(=O)C)[O:32][C@@H:31]1Br)(=O)C.[OH-].[Na+]>CC(C)=O>[C@@H:31]1([O:1][C:2]2[CH:23]=[CH:22][C:5]([C:6]3[O:7][C:8]4[C:13]([C:14](=[O:18])[C:15]=3[O:16][CH3:17])=[C:12]([OH:19])[CH:11]=[C:10]([O:20][CH3:21])[CH:9]=4)=[CH:4][C:3]=2[O:24][CH3:25])[O:32][C@H:33]([CH2:44][OH:45])[C@@H:34]([OH:40])[C@H:35]([OH:36])[C@H:30]1[OH:29]

Komponenten

5

Edukt 3

HCID 14798Sodium Hydroxide2×HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 5281677Pachypodol

Produkt 1

HCID 54187119HCID 54187119, VerbindungAusbeute 106,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To an ice-cooled solution containing 250 mg of 4',5-dihydroxy-3,3',7-trimethoxyflavone in 10 ml of acetone were alternately added a solution of 400 mg of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in 10 ml of acetone, and 5 ml of 0.8% aqueous sodium hydroxide over 30 minutes, while stirring. After allowing the reaction mixture to stand at room temperature for 3 hours, 20 ml of 0.2% aqueous sodium hydroxide were added thereto. Stirring was continued at room temperature for 3 hours, during which time crystallization took place. The crystals were collected by filtration and recrystallized from ethanol to give 390 mg (80% yield) of 4'-(β-D-glucopyranosyloxy)-5-hydroxy-3,3',7-trimethoxyflavone as pale yellow needles: m.p. 203°-204° C.

Aufarbeitung

  1. stirringStirring
  2. customwas continued at room temperature for 3 hours, during which time crystallization
  3. filtrationThe crystals were collected by filtration
  4. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-49a6629c73304c02a55efa2c0ae4ea4d
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04352792

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