3-(4-Methoxyphenyl)oxolan-2-one → 3-(4-Methoxycyclohexyl)-dihydro-furan-2-one

HRID 1670832Notes

Reaction equation

HRID 1670832 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])=[CH:5][CH:4]=1>[Rh].C(O)C>[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][CH:6]([CH:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])[CH2:7][CH2:8]1

Participants

4

Reactant 1

HCID 220132323-(4-Methoxyphenyl)oxolan-2-one

Product 1

HCID 673560023-(4-Methoxycyclohexyl)-dihydro-furan-2-oneYield 91%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Stir a mixture of 3-(4-methoxyphenyl)-dihydro-furan-2-one (0.98 g), rhodium on carbone (5%, 0.98 g) and ethanol (50 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 0.92 g (90%) 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-943707f5bb404627b7890ff4369fde0e
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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