Imidazolium salts as phase transfer catalysts for the dialkylation and cycloalkylation of active methylene compounds

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 635-638

  Muthusamy, Sengodagounder ^a   Gnanaprakasam, Boopathy ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Alkylation; Imidazolium cations; Ionic liquid; Phase transfer catalysts

Indexed keywords

CARBENOID; IMIDAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 11144269655     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.141     Document Type: Article

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22. General procedure for the dialkylation and cycloalkylation reactions using imidazolium salts as PTCs: To a vigorously stirred solution of active methylene compound (20.0 mmol) and powdered anhydrous potassium carbonate (50.0 mmol) in DMF (50.0 mL) was added the appropriate dihaloalkane (22.0 mmol). To this reaction mixture a catalytic amount of imidazolium salt (2.0 mmol) was added and the mixture stirred at room temperature for the appropriate time. The reaction mixture was filtered and the solid washed with diethyl ether. The filtrate was diluted with water (200 mL) and extracted with diethyl ether (4 × 75 mL). The organic layers were combined and washed with brine solution. Finally, evaporation of the organic layer afforded the crude product, which was chromatographed through a short alumina column (10% EtOAc/hexane) to yield the respective pure products
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