Triethylamine → HCID 67136300, Verbindung

HRID 230928

Reaktionsgleichung

Reaktionsgleichung von HRID 230928
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:30]2[C:31](/[CH:34]=[CH:35]/[C:36]3[CH:41]=[CH:40][C:39](Br)=[CH:38][CH:37]=3)=[CH:32][O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2].[C:43]([OH:48])(=[O:47])[CH2:44][CH:45]=[CH2:46].C(N(CC)CC)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:30]2[C:31](/[CH:34]=[CH:35]/[C:36]3[CH:41]=[CH:40][C:39](/[CH:46]=[CH:45]/[CH2:44][C:43]([OH:48])=[O:47])=[CH:38][CH:37]=3)=[CH:32][O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 327433-Butenoic acidHCID 80271Tri-o-tolylphosphineHCID 67136339HCID 67136339, Verbindung

Produkt 1

HCID 67136300HCID 67136300, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[(E)-2-(4-bromophenyl)vinyl]benzofuran (0.2 g), 3-butenoic acid (0.053 mL), triethylamine (0.22 mL), palladium (II) acetate (7 mg) and tris(2-methylphenyl)phosphine (19 mg) in acetonitrile (4 mL) was heated for reflux under an argon atmosphere for 8 hours. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. The filtrate was diluted with ethyl acetate. The solution was washed with 0.5 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-dichloromethane/methanol=20/1) to give the title compound (0.17 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperaturefor reflux under an argon atmosphere for 8 hours
  3. customthe insoluble material was removed by filtration
  4. additionThe filtrate was diluted with ethyl acetate
  5. washThe solution was washed with 0.5 mol/L hydrochloric acid, water and brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-dichloromethane/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-07c69205900345098a65ea91cce9e470
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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