Reaction #2045064

Reaction equation

water

ethyl 4-(2,2,3-trimethylcyclopent-3-enyl)but-2-enoate ethyl 4-(2,2,3-trimethylcyclopentenyl)butanoic acid

→

ethyl 4-(2,2,3-trimethylcyclopentyl)butanoate ethyl 4-(2,2,3-trimethylcyclopentyl)butanoic acid

Yield 74.0%

Solvents

Ethyl Acetate

Conditions

Workup

1. 1
   OtherTo 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. 2
   workup.ADDITIONwas added as catalyst
3. 3
   workup.ADDITIONwas added to the reaction flask
4. 4
   OtherThe flask was flushed with hydrogen
5. 5
   workup.ADDITIONwere refilled
6. 6
   FiltrationThe reaction mixture was filtered through a celite plug
7. 7
   ConcentrationThe organic layers were concentrated in vacuo
8. 8
   Otherpurified via flash column chromatography AcOEt/Hexanes (gradient 0 to 40%)

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.

Source