HCID 18548286, compound → HCID 18548283, compound

HRID 1266003Notes

Reaction equation

HRID 1266003 reaction equation
[C:1]1([C:6]2([CH2:12][C:13]([CH3:15])=[CH2:14])[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3][CH:2]=1>C(OCC)(=O)C.C(O)C.[Pd]>[CH:1]1([C:6]2([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 18548286HCID 18548286, compound

Product 1

HCID 18548283HCID 18548283, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of the compound of Embodiment 4 (2-cyclopent-1-enyl-2-(2-methylprop-2-enyl)cyclopentan-1-one, 5.0 g, 0.02 moles) in ethyl acetate/ethanol (9:1, 100 mL) was added to a Parr reaction bottle. To this vessel was added 5% Pd—C (0.5 g) in one portion. The reaction vessel was placed in a Parr hydrogenation apparatus and H2 gas (40 psi) was introduced. The apparatus was agitated for 2 hours, and it was determined by TLC and GC that the reaction was complete. The resulting organic slurry was filtered through celite and concentrated. The pale yellow oil was distilled under vacuum to give 2-cyclopentyl-2-(2-methylpropyl)-cyclopentan-1-one (4.24 g, 83.1% yield).

Workup

  1. additionwas introduced
  2. filtrationThe resulting organic slurry was filtered through celite
  3. concentrationconcentrated
  4. distillationThe pale yellow oil was distilled under vacuum

Sources & evidence

ORD record
ord-a17f3576b92f4b4cb41c4d8c6fdfdbf7
Source dataset
uspto-grants-2003_04
Patent number
US06548474B1

Reaction notes

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