HCID 15544964, compound → HCID 9855473, compound

HRID 985743Notes

Reaction equation

HRID 985743 reaction equation
[CH2:1]([C@@H:4]1[CH2:8][C:7](=[O:9])[CH:6]=[CH:5]1)[CH2:2][CH3:3]>[Pd].C(OCC)(=O)C.[H][H]>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C:7](=[O:9])[CH2:8]1)[CH2:2][CH3:3]

Participants

5

Reactant 1

HCID 15544964HCID 15544964, compound

Product 1

HCID 9855473HCID 9855473, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 2 (1.2 g, 9.7 mmol) and 10% palladium on charcoal (catalytic quantity) in ethyl acetate (30 ml) was shaken in hydrogen at 55 psi and at 30° C. for 6 hours. The reaction mixture was filtered and the solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, pentane-ether, 1:0 to 9:1) to give the 3-propylcyclopentanone 3 (1.07 g, 88%). νmax(film)/cm−1 1744 (C═O).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was chromatographed (SiO2, pentane-ether, 1:0 to 9:1)

Sources & evidence

ORD record
ord-97a5e66bf2494492b5dc9d63a35d2abf
Source dataset
uspto-grants-2005_03
Patent number
US06872856B2

Reaction notes

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