The unsaturated ketones (I) are transformed into the tribromo derivatives (II) which react in situ with methylate to produce the isomeric esters (V) and (VI).
The stereoisomeric 4‐methyl‐2,4‐pentadienoates (IV) and (V) are prepared by three different methods: Bromination of mesityl oxide (I) to give the tribromide (II) and subsequent sodium methoxide (III) induced Favorskii rearrangement yield the Z‐isomer (IV) as the main product, whereas direct treatment of the bromide with triethylamine in methanol (VII) predominantly produces the E‐isomer (V).
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