Dimethylformamide → 5-[(4-Chlorophenyl)methylidene]-2,2-dimethylcyclopentan-1-one

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Reaction Steps

2.4 g of sodium hydride (60% oily sodium hydride washed with anhydrous benzene) was added to 100 ml of anhydrous dimethylformamide under nitrogen atmosphere while stirring. 24 g of 2-(4-chlorobenzylidene)-5-methylcylopentanone (prepared in Example 3) was added to the mixture, followed by stirring at room temperature until generation of hydrogen was terminated. After the addition of 15 g of methyl iodide, the mixture was stirred for a further 2 hours at 60° C. The reaction mixture thus obtained was allowed to cool, poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure. The residue was solidified with the addition of a small amount of hexane to obtain the title compound.

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