反応 #2045064

反応方程式

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

収率 74.0%

溶媒

Ethyl Acetate

反応条件

後処理

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

実験手順

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.

出典