Butyloct-2-enal

Reduction of methyl (2 )-2-butyl-3-pentyl-propenoate (60) yielded the corresponding alcohol 61 in 92% yield. Upon oxidation of alcohol 61, the product 62 was furnished in 87% yield. 

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Das et al. have explored the reaction of MBH acetates with unactivated alkyl halides in the presence of Zn in saturated aqueous NH4CI solution to afford stereoselective trisubstituted olefins. The reactions of 3-hydroxy-2-methylene-alkanoates 220 gave (2 )-2-substituted-alk-2-enoates 222 exclusively, whereas the reactions of 3-hydroxy-2-methylene-alkanenitriles 221 afforded (2Z)-2-substituted-alk-2-enenitriles 223 as major products with high ( -selectivity (Scheme 3.88). The methodology was successfully applied to the synthesis of (2 )-2-butyloct-2-enal 224, an alarm pheromone component of the African weaver ant, Oecophylla longinoday ... 

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