Abstract
Reaction of (ethoxycarbonylfuryl)methanephosphonates with diethyl carbonate in presence of sodium foil is studied. It is shown that if the acidifying group is conjugated with the carbanion center of 2-furylmethanephosphonate, addition of the carbanion to the carbonyl group of diethyl carbonate takes place to give 2-furylacetic acid derivatives in high yield. Sodium salts of these CH-acids are synthesized, isolated, and characterized. Their alkylation with alkyl bromoacetates is carried out. If ethoxycarbonyl group is not conjugated with the carbanion center, conversion of starting phosphonate and yield of adduct sharply decreases. Alkyl (2- and 4-ethoxycarbonylfur-3-yl)methanephosphonates immediately after acylation with diethyl carbonate are reduced with sodium-diethyl carbonate system to form alkyl 1-(2- and 4-ethoxycarbonylfur-3-yl)-ethanephosphonates. Formation of intermediate reduction product, the phosphorylated furylacetic aldehyde is also fixed spectroscopically. Simultaneously with the reduction dealkylation of ester group of starting phosphonates and alkyl 1-(3-furyl)ethanephosphonates takes place leading to the carboxylic acid salts. Alkyl (2-methyl-5-ethoxycarbonylfur-3-yl)methanephosphonate does not take part in condensation. It gives only the products of dealkylation under the action of sodium ethylate forming from diethyl carbonate.
Similar content being viewed by others
References
Pevzner, L.M., Russ. J. Gen. Chem., 2012, vol. 82, no. 12, p. 1938. DOI: 10.1134/S1070363212120067.
Pevzner, L.M., Russ. J. Gen. Chem., 2013, vol. 83, no. 9, p. 1687. DOI: 10.1134/S1070363213090107.
Pevzner, L.M., Russ. J. Gen. Chem., 2014, vol. 84, no. 42, p. 658. D0I: 10.1134/S1070363214040100.
Pevzner, L.M., Russ. J. Gen. Chem., 2006, vol. 76, no. 4, p. 621. D0I: 10.1134/S1070363206040207.
Pevzner, L.M., Russ. J. Gen. Chem., 2006, vol. 76, no. 8, p. 1299. D0I: 10.1134/S107036320608024X.
Pevzner, L.M., Russ. J. Gen. Chem., 2011, vol. 81, no. 1, p. 56. D0I: 10.1134/S1070363211010099.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © L.M. Pevzner, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 7, pp. 1143–1153.
Rights and permissions
About this article
Cite this article
Pevzner, L.M. Reaction of (ethoxycarbonylfuryl)methanephosphonates with diethyl carbonate in presence of sodium foil. Russ J Gen Chem 84, 1339–1348 (2014). https://doi.org/10.1134/S1070363214070159
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363214070159