Ammonium formate → T-1095

HRID 1003937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003937
[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]CC=C)=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][C:37]([O:39][CH3:40])=[O:38])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2.C([O-])=O.[NH4+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][C:37]([O:39][CH3:40])=[O:38])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 21967943HCID 21967943, Verbindung

Produkt 1

HCID 6918410T-1095Ausbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-(5-Benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (470 mg) is dissolved in acetonitrile (7 ml), and thereto are added dichlorobis(triphenylphosphine)-palladium (II) (17.7 mg,) and ammonium formate (319 mg), and the mixture is heated under reflux overnight. After cooling, the insoluble materials are removed by filtration, and the filtrate is concentrated. To the residue are added ethyl acetate and water, and the mixture is shaken. The organic layer is separated, washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (370 mg).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customthe insoluble materials are removed by filtration
  5. concentrationthe filtrate is concentrated
  6. additionTo the residue are added ethyl acetate and water
  7. customThe organic layer is separated
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-8e587278fae74a85b742becb3303a20c
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048842

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