Synthesis of E-9-dodecen-l-yl acetate using organomanganese reagents

The Grignard reagent obtained from 2-(6-bromohexyloxy)-tetrahydropyrane, by treatment with anhydrous manganese(II) chloride was transformed to the cor responding organomanganese reagent, which was coupled with E-1-bromo-3-hexe ne by treatment with anhydrous manganese chloride. Further deprotection and acetylation furnished E-9-dodecen-1-yl acetate. A second procedure involve d the coupling of E-3-hexenylmanganese bromide and 6-bromohexyl acetate. Co upling reactions were carried out at 0 degrees C, using tetrahydrofurane an d N-methylpyrrolidone as co-solvent.