Citric Acid → HCID 21967943, Verbindung

HRID 1003936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003936
[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][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[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.CC(C)=O.Cl[C:45]([O:47][CH3:48])=[O:46].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C(C)=CC(C)=CC=1C.ClCCl>[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][CH2:21][CH:22]=[CH2:23])=[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:45]([O:47][CH3:48])=[O:46])[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

7

Edukt 4

HCID 311Citric AcidHCID 6586Methyl chloroformateHCID 10601391HCID 10601391, VerbindungHCID 18522661Acetone cardice

Produkt 1

HCID 21967943HCID 21967943, VerbindungAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 79532,4,6-TrimethylpyridineLösungsmittel

Versuchsvorschrift

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (500 mg) is dissolved in 2,4,6-collidine (5 ml), and the mixture is cooled to 40° C. with dry ice-acetone, and thereto is added dropwise a solution of methyl chloroformate (114 mg) in dichloromethane (0.5 ml) with stirring. The mixture is stirred at 40° C. for one hour, and stirred at room temperature for 1.5 hour. The reaction mixture is poured into cold 10% aqueous citric acid solution, 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'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (487 mg).

Aufarbeitung

  1. stirringThe mixture is stirred at 40° C. for one hour
  2. stirringstirred at room temperature for 1.5 hour
  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-2e55ee8970be49a6a8b07a7ae20e825a
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048842

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