Abstract
Synthesis of methyl 4-isopropyl-7-methyl-5, 7-octadienoate (4) from readily available starting materials are described. Method A : Methyl 4-formyl-5-methylhexanoate (2) was prepared from the reaction of the piperidine enamine of isovaleraldehyde and methyl acrylate. A Wittig reaction between (2) and methallyli denetriphenylphosphorane in anhydrous tetrahydrofuran gave predominantly compound (4). Method B : A Wittig reaction of between 4-cyano-2-isopropyl butyraldehyde (3) and methallylidene-triphenylphosphorane gave 4-isopropyl-7-methyl-5, 7 - octadienenitrile (5). Hydrolysis of (5) under basic conditions gave a mixture of (4) and isomers of (4).
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