Coupling of Metallated Ethyl Vinyl Ether with Nonyl Bromide and Acetone

2 Coupling of Metallated Ethyl Vinyl Ether with Nonyl Bromide and Acetone 

This procedure gives typical reaction conditions for the alkylation and hydroxy-alkylation of alkyl vinyl ethers via the 1-potassio- and 1-lithio derivatives, respectively. The alkylation of the potassium compounds with alkyl bromides proceeds smoothly at temperatures in the region of —40 °C. Alkylation is often accompanied by dehydrohalogenation. In the experiment described below the ratio alkylation dehydrohalogenation is high. Under similar conditions vinylpotassium H2C=CH—K gave a much lower yield of the alkylation product (1-decene) in its 

Couplings of potassium compounds with enolizable carbonyl compounds give often low yields owing to formation of enolates. With lithium and Grignard compounds the results are mostly satisfactory. 

The reaction with cyclopentanone is carried out in a similar way and affords the corresponding carbinol as a solid in 80% yield (Note 3). 

Since nonyl bromide and the product cannot be separated by distillation, a short measure of the alkyl halide is added. 

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