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Low-Temperature Reactions of α-Bromopropanoyl Chloride with Lithium Derivative of Ethyl Acetate

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Abstract

The reaction of 2-bromopropanoyl chloride with lithium ethyl acetate generated in situ by the reaction of equimolar amounts of lithium diisopropylamide with ethyl acetate forms, depending on the conditions (temperature, time, reagent ratio), diethyl 2,2′-(3-methyloxirane-2,2-diyl)diacetate, 2,2-dibromo-N,N-diisopropylpropanamide, and ethyl (5-methyl-4-oxo-4,5-dihydrofuran-2-yl)acetate as minor by-products along with the expected acylation product ethyl 4-bromo-3-oxopentanoate. The reaction with 2 or 5 equiv of lithium ethyl acetate (–78°C → –20°C) gave, together with the mentioned α-bromo ester, ethyl (5-methyl-4-oxo-4,5-dihydrofuran-2-yl)acetate formed as a result of transformations of the adduct of the second LiCH2CO2Et molecule and ethyl-4-bromo-3-oxopentanoate. The reaction 2-bromopropanoyl chloride with sodium malonic ester involves acylation of enol form of the primary expected acylation product to afford dimethyl |2-bromo-1-[(2-bromopropanoyl)oxy]propylidene-malonate.

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Acknowledgments

Analyses were performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Ufa Research Center, Russian Academy of Sciences.

Funding

The work was financially supported by the Russian Science Foundation (project no. 15-13-00039-P).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, Republic of Bashkortostan, 450054, Russia

    Z. R. Valiullina, L. S. Khasanova, A. M. Galeeva, N. K. Selezneva & M. S. Miftakhov

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  1. Z. R. Valiullina
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  2. L. S. Khasanova
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  3. A. M. Galeeva
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  4. N. K. Selezneva
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  5. M. S. Miftakhov
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Corresponding author

Correspondence to M. S. Miftakhov.

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The authors declare no conflict of interest.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 11, pp. 1762–1767.

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Valiullina, Z.R., Khasanova, L.S., Galeeva, A.M. et al. Low-Temperature Reactions of α-Bromopropanoyl Chloride with Lithium Derivative of Ethyl Acetate. Russ J Org Chem 55, 1726–1730 (2019). https://doi.org/10.1134/S1070428019110137

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  • DOI: https://doi.org/10.1134/S1070428019110137

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