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

HRID 1461959Notes

Reaction equation

HRID 1461959 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

HCID 20454258HCID 20454258, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5c01f156bce94b3f85b9c16279e09218
Source dataset
uspto-grants-1984_07
Patent number
US04457862

Reaction notes

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