2-[1-Methyl-2-methylidene-3-(prop-1-en-2-yl)cyclopentane-1-carbonyl]cyclopentan-1-one → HCID 20454258, Verbindung

HRID 1461959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461959
[CH3:1][C:2]1([C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([CH3:9])=[CH2:8])[C:3]1=[CH2:10]>[Pd]>[CH3:1][C:2]1([C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])=[O:12])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:8])[CH3:9])[CH:3]1[CH3:10]

Komponenten

3

Edukt 1

HCID 30200112-[1-Methyl-2-methylidene-3-(prop-1-en-2-yl)cyclopentane-1-carbonyl]cyclopentan-1-one

Produkt 1

HCID 20454258HCID 20454258, VerbindungAusbeute 17,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

9.6 g of 2-[1-methyl-2-methylene-3-(prop-1-en-2-yl)-cyclopentylcarbonyl]-cyclopentanone are treated in 100 ml of absolute alcohol with 1 g of 5% palladium-on-carbon and the mixture is hydrogenated at normal pressure. After completion of the hydrogen uptake (8 hours), the mixture is filtered, the filtrate is concentrated and the residue is chromatographed on a hundred-fold amount of silica gel with toluene/ethyl acetate (1:2). There are obtained 1.7 g of 2-(1,2-dimethyl-3-isopropyl-cyclopentylcarbonyl)-cyclopentanone, which are contaminated with a small amount (<5%) of 2-(1,2-dimethyl-3-isopropyl-cyclopent-2-en-1-yl-carbonyl)-cyclopentanone or 2-(1,2-dimethyl-3-isopropylidenecyclopentyl carbonyl)-cyclopentanone.

Aufarbeitung

  1. filtrationAfter completion of the hydrogen uptake (8 hours), the mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customthe residue is chromatographed on a hundred-fold amount of silica gel with toluene/ethyl acetate (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-5c01f156bce94b3f85b9c16279e09218
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04457862

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