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Glutaric anhydride → 4-[4-(3,5-Dioxohexyl)phenylcarbamoyl]butyric acid

HRID 1402660
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1402660
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])=[CH:6][CH:5]=1)([O-])=O.[O:18]1[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][C:19]1=[O:25]>O1CCCC1>[O:17]=[C:12]([CH2:13][C:14](=[O:16])[CH3:15])[CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([NH:1][C:23]([CH2:22][CH2:21][CH2:20][C:19]([OH:25])=[O:18])=[O:24])=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 7940Glutaric anhydrideHCID 18717149HCID 18717149, Verbindung

Produkt 1

HCID 187171484-[4-(3,5-Dioxohexyl)phenylcarbamoyl]butyric acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

200 mL tetrahydrofuran, 6-(4-nitro-phenyl)-hexane-2,4-dione (8.0 g, 34.0 mmol) and dihydro-pyran-2,6-dione (3.88 g, 34.0 mmol) were added to a reaction vessel. The reaction vessel was purged three times with argon. Approximately 200 mg palladium (10 wt % on activated carbon) was added. The reaction vessel was purged again with argon and excess hydrogen introduced via a balloon. Solution stirred 16 hours at room temperature. Hydrogen removed under reduced pressure and catalyst removed by filtration through celite. Tetrahydrofuran removed under reduced pressure to afford title compound (10.5 g, 97%, yellow solid).

Aufarbeitung

  1. customThe reaction vessel was purged three times with argon
  2. additionApproximately 200 mg palladium (10 wt % on activated carbon) was added
  3. customThe reaction vessel was purged again with argon and excess hydrogen
  4. additionintroduced via a balloon
  5. customHydrogen removed under reduced pressure and catalyst
  6. customremoved by filtration through celite
  7. customTetrahydrofuran removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1338307455b3423a81ce8dd3bf4d5b8f
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08912148B2

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