3-Phenyloxolan-2-one → 3-Cyclohexyl-dihydro-furan-2-one

HRID 1670811Notes

Reaction equation

HRID 1670811 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][O:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Rh].C(O)C>[CH:1]1([CH:7]2[CH2:11][CH2:10][O:9][C:8]2=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 232693-Phenyloxolan-2-one

Product 1

HCID 220132343-Cyclohexyl-dihydro-furan-2-oneYield 92.1%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Stir a mixture of 3-phenyl-dihydro-furan-2-one (9.0 g), rhodium on carbone (5%, 3.62 g) and ethanol (220 mL) on a hydrogenation parr shaker at 60 psi, 60° C. for 18 hours. Remove the reaction from the parr shaker and filter the mixture through celite, concentrate the filtrate to afford 8.6 g (92%) of the title compound.

Workup

  1. customRemove
  2. customthe reaction from the parr shaker
  3. filtrationfilter the mixture through celite
  4. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-1b2ddf76b64c4c319bb096b1f34f8ec6
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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