ChemicalBook CAS DataBase List PENTENYL CYCLOPENTANONE

PENTENYL CYCLOPENTANONE synthesis

5synthesis methods

Product Name:PENTENYL CYCLOPENTANONE
CAS Number:2520-60-7
Molecular formula:C10H16O
Molecular Weight:152.23

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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