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HCID 49806006, Verbindung → HCID 68555156, Verbindung

HRID 1854704
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1854704
[CH3:1][N:2]([CH3:27])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:26])[CH2:12][C:13](=[O:25])/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:27][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:26])[CH2:12][C:13](=[O:25])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[CH:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 49806006HCID 49806006, Verbindung

Produkt 1

HCID 68555156HCID 68555156, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1E,6E)-1-(4-dimethylaminophenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (15 mg, 41 μmol, synthesized in Example 9) in 3.0 mL of ethyl acetate was added palladium 5% on carbon (30 mg) under nitrogen. After the vessel was purged with hydrogen, the reaction mixture was stirred under 1 atm of hydrogen at room temperature for 1.5 h. After the vessel was purged with nitrogen, the reaction mixture was filtered to remove palladium 5% on carbon. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 65/35) to obtain the title compound as a gum (8.0 mg, 53%) having the following characteristics.

Aufarbeitung

  1. customAfter the vessel was purged with hydrogen
  2. customAfter the vessel was purged with nitrogen
  3. filtrationthe reaction mixture was filtered
  4. customto remove palladium 5% on carbon
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 65/35)

Quellen und Nachweise

ORD-Eintrag
ord-ef1bf5dab967432c9542c62565a0a72f
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08962674B2

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