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Synthesis of methyl 3-bromomethylbut-3-enoate and its reactions with aldehydes and tributylchlorostannane in the presence of zinc

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Abstract

Methyl 3-bromomethylbut-3-enoate smoothly reacted with prenal, β-ionylideneacetaldehyde, benzyloxyacetaldehyde, and tributylchlorostannane in the presence of zinc and aqueous ammonium chloride in tetrahydrofuran to give the corresponding δ-hydroxy-β-methylidenecarboxylic acid esters. In the absence of ammonium chloride, satisfactory yields of the products were obtained only in the reactions with prenal and benzyloxyacetaldehyde; these reactions involved lactonization of intermediate δ-hydroxy-β-methylidenecarboxylic acid esters, and the double carbon-carbon bond migrated to the conjugated position with the lactone carbonyl group. The condensation of β-ionylideneacetaldehyde with methyl 3-bromomethylbut-3-enoate was successfully used to obtain isotretinoin. Initial methyl 3-bromomethylbut-3-enoate was synthesized in a good yield from readily accessible ethyl 3,3-diethoxypropionate via cyclopropanation with ethylmagnesium bromide in the presence of titanium tetra(isopropoxide), oxidation of the acetal moiety to ester, and cleavage of the cyclopropane ring in intermediate methyl (1-methylsulfonyloxycyclopropyl)acetate.

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Authors and Affiliations

  1. Belarussian State University, pr. Nezavisimosti 4, Minsk, 220030, Belarus

    I. V. Mineeva & O. G. Kulinkovich

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  1. I. V. Mineeva
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  2. O. G. Kulinkovich
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Correspondence to O. G. Kulinkovich.

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Original Russian Text © I.V. Mineeva, O.G. Kulinkovich, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 9, pp. 1277–1282.

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Mineeva, I.V., Kulinkovich, O.G. Synthesis of methyl 3-bromomethylbut-3-enoate and its reactions with aldehydes and tributylchlorostannane in the presence of zinc. Russ J Org Chem 44, 1261–1266 (2008). https://doi.org/10.1134/S1070428008090029

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  • DOI: https://doi.org/10.1134/S1070428008090029

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