Water → HCID 86647265, compound

HRID 1957882Notes

Reaction equation

HRID 1957882 reaction equation
O.[CH3:2][C:3]1([CH3:17])[C:7]([CH3:8])=[CH:6][CH2:5][CH:4]1[CH2:9][CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH2:18]([CH:20]([CH2:24][CH2:25][C:26]1[C:27]([CH3:33])([CH3:32])[CH:28]([CH3:31])[CH2:29][CH:30]=1)[C:21]([OH:23])=[O:22])[CH3:19]>C(OCC)(=O)C>[CH3:17][C:3]1([CH3:2])[CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH2:18]([CH:20]([CH2:24][CH2:25][CH:26]1[CH2:30][CH2:29][CH:28]([CH3:31])[C:27]1([CH3:32])[CH3:33])[C:21]([OH:23])=[O:22])[CH3:19]

Participants

4

Reactant 2

HCID 962WaterHCID 86647266HCID 86647266, compound

Product 1

HCID 86647265HCID 86647265, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a three necked round bottom flask with a stir bar flushed with nitrogen, Degussa type palladium on charcoal Pd/C (1.5 g, 10% Pd) was added as catalyst. The catalyst was covered with distilled water (8 ml) and ethyl 4-(2,2,3-trimethylcyclopent-3-enyl)but-2-enoate/ethyl 4-(2,2,3-trimethylcyclopentenyl)butanoic acid (10.0 g, 44.9 mmol) in Ethyl Acetate (AcOEt) (200 ml) was added to the reaction flask. The flask was flushed with hydrogen and the reaction was run under hydrogen balloons that were refilled as needed. After 17 h at room temperature the reaction was found to be completed by gas chromatography and mass spectrometry (GCMS). The reaction mixture was filtered through a celite plug. The organic layers were concentrated in vacuo and purified via flash column chromatography AcOEt/Hexanes (gradient 0 to 40%) to give ethyl 4-(2,2,3-trimethylcyclopentyl)butanoate/ethyl 4-(2,2,3-trimethylcyclopentyl)butanoic acid as a colorless oil (7.48 g, 74%). The NMR data is indicated below.

Workup

  1. customTo a three necked round bottom flask with a stir bar flushed with nitrogen, Degussa type palladium on charcoal Pd/C (1.5 g, 10% Pd)
  2. additionwas added as catalyst
  3. additionwas added to the reaction flask
  4. customThe flask was flushed with hydrogen
  5. additionwere refilled
  6. filtrationThe reaction mixture was filtered through a celite plug
  7. concentrationThe organic layers were concentrated in vacuo
  8. custompurified via flash column chromatography AcOEt/Hexanes (gradient 0 to 40%)

Sources & evidence

ORD record
ord-5af7a01105634dac880fc87a38e6b632
Source dataset
uspto-grants-2013_04
Patent number
US08409649B2

Reaction notes

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