PENTENYL CYCLOPENTANONE synthesis
- Product Name:PENTENYL CYCLOPENTANONE
- CAS Number:2520-60-7
- Molecular formula:C10H16O
- Molecular Weight:152.23
Yield:2520-60-7 72%
Reaction Conditions:
with palladium diacetate;triphenylphosphine;zinc dibromide in dichloromethane; for 5 h;Inert atmosphere;Reflux;regioselective reaction;
Steps:
General procedure for the synthesis of homoallyl ketones: Preparation of 2-allylcyclohexanone (4a)
General procedure: Under nitrogen, a mixture of allylic alcohol 3a (1.5mmol), Pd(OAc)2 (13mg, 0.06mmol), PPh3 (63mg, 0.24mmol), and ZnBr233 (0.90g, 4mmol) was heated at reflux in CH2Cl2 (10mL) for 15min. Next, a solution of enamine 2b (7.5mmol) in CH2Cl2 (5mL) was added, and the reaction mixture heated at reflux for 2-18h. After the evaporation of CH2Cl2, water (10mL) was added with NaOH (1M, 30mL), and the mixture extracted with CH2Cl2 (3×30mL). The organic phase was washed with saturated ammonium chloride (10mL) and dried over MgSO4. After solvent removal, the residue was subjected to column chromatography (petroleum-ether/ether=9:1) to give homoallyl ketone 4a as a colorless oil (165mg, 80%).
References:
Bouhalleb, Ghalia;Mhasni, Olfa;Poli, Giovanni;Rezgui, Farhat [Tetrahedron Letters,2017,vol. 58,# 26,p. 2525 - 2529] Location in patent:supporting information
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