Abstract
Reactions of furyl(diethoxyphosphoryl)acetic aldehyde containing ester or cyano group in the furan ring with ethoxycarbonylmethylenetriphenylphosphorane has been shown to afford alkyl E-4-(furyl)-4-(diethoxyphosphoryl)but-3(2)-enoates. When treated with potassium tert-butoxide the mixture of alkyl E-4-(3-ethoxycarbonylfur-2-yl)-4-(diethoxyphosphoryl)but-2-enoate and -but-3-enoate gives a potassium salt of CHacid. Its acidifying results in a mixture of starting compounds with a larger amount of -but-3-enoate. Under analogous conditions the mixture of alkyl E-4-(2-ethoxycarbonylfur-3-yl)-4-(diethoxyphosphoryl)but-2-enoate and -but-3-enoate undergoes cyclization to a phosphorylated derivative of alkyl 7-hydroxybenzofuran-6-carboxylate. The cyclization of the mixture of alkyl E-4-(4-ethoxycarbonylfur-3-yl)-4-(diethoxyphosphoryl)but-2-enoate and -but-3-enoate gives analogous derivative of isobenzofuran.
Similar content being viewed by others
References
Doronina, E.P., Pevzner, L.M., Polukeev, V.A., and Petrov, M.L., Russ. J. Gen. Chem., 2017, vol. 87, no. 3, p. 447. doi 10.1134/S1070363217o30136
Pevzner, L.M., Russ. J. Gen. Chem., 2016, vol. 86, no. 8, p. 1864. doi 10.1134/S1070363216080156
Pevzner, L.M., Russ. J. Gen. Chem., 2012, vol. 82, no. 12, p. 1938. doi 10.1134/S1070363212120067
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © L.M. Pevzner, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 7, pp. 1123–1133.
Rights and permissions
About this article
Cite this article
Pevzner, L.M. Derivatives of furyl(diethoxyphosphoryl)acetic aldehyde in Wittig reaction. Russ J Gen Chem 87, 1516–1526 (2017). https://doi.org/10.1134/S107036321707012X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107036321707012X