Process for the preparation of trans-3-formylbut-2- enenitrile

Details Process for the preparation of trans-3-formylbut-2- enenitrile Process for the preparation of trans-3-formylbut-2- enenitrile

C - Chemistry, Metallurgy

07

F

260/352.3, 260/5

C07F 7/18 (2006.01) C07D 319/06 (2006.01)

Patent

CA 1172644

ABSTRACT OF THE DISCLOSURE A process is provided for the preparation of trans-3-formylbut- 2-enenitrile (V), a key intermediate in the synthetic pathway leading to trans-zeatin (I) and dihydrozeatin (II), both of which are naturally occurring cytokinins. The process involves a base catalyzed condensation of a dialkyl or cyclic acetal of pyruvaldehyde (III) with acetonitrile to yield the corresponding dialkyl or cyclic acetal of 3-formylbut-2- enenitrile (IV). The reaction proceeds regioselectively to form the favoured trans-isomer in good yield. The .alpha.,.beta.-unsaturated nitrile thus formed is hydrolyzed under acidic conditions to yield trans-3-formylbut- 2-enenitrile (V), which can be easily distilled without contamination of the cis-isomer. The trans-3-formylbut-2-enenitrile can be selectively or exhaustively reduced to form either trans-3-hydroxymethylbut-2- enylamine (VI) or 3-hydroxymethylbutylamine (VII), which compounds can be condensed with 6-chloropurine (IX) by known methods to form trans-zeatin or dihydrozeatin respectively.

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