Allyl bromide → HCID 10601391, Verbindung

HRID 1003935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003935
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([OH:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[O:22][C@@H:23]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]3[OH:25])=[O:13])[CH:8]=[CH:9][C:2]1=2.C(=O)([O-])[O-].[K+].[K+].[CH2:40](Br)[CH:41]=[CH2:42]>CC(C)=O>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:42][CH:41]=[CH2:40])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[O:22][C@@H:23]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]3[OH:25])=[O:13])[CH:8]=[CH:9][C:2]1=2

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6918439T-1095A

Produkt 1

HCID 10601391HCID 10601391, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (2.50 g) is dissolved in acetone (20 ml), and thereto are added potassium carbonate (2.13 g) and allyl bromide (933 mg), and the mixture is refluxed for 6 hours. After cooling, the reaction mixture is poured into ice-water, and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (1.63 g).

Aufarbeitung

  1. temperaturethe mixture is refluxed for 6 hours
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-22413ed291b94becb6f3eb1d406f315a
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048842

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