Heptylmagnesium bromide

By a similar procedure benzylmagnesium chloride and 2,3-dibromopropene give 4-phenyl-2-bromobutene-i in about 45 per cent yield, b.p. ii9°/20 mm. and heptylmagnesium bromide and 2,3-dibromopropene give 2-bromodecene-i in 60-65 per cent yields, b.p. 76-77°/3 mm. 

The potentiality of the present methodology is demonstrated by the synthesis of y-undecalactone, as shown in Scheme 18 [37,47], The treatment of the THP-protected cu-hydroxyalkyl iodide with the anion of methoxybis(trimethylsilyl) methane gave the corresponding alkylation product. Acidic deprotection of the hydroxyl group followed by Swern oxidation produced the aldehyde. The aldehyde was allowed to react with heptylmagnesium bromide, and the resulting alcohol was protected as tm-butyldimethylsilyl ether. The electrochemical oxidation in methanol followed by the treatment with fluoride ion afforded the y-undeealactone. 

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