Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 377–378 | Cite as

Unusual route of hydrogenation of diethyl (4R)-[(4-hydroxy-4,5-dihydrofuran-2-yl)methyl]-phosphonate

  • V. K. BrelEmail author

It has previously been shown that diethyl (4R)-(4,5-dihydroxypenta-1,2-dienyl)phosphonate (1) undergoes an intramolecular cyclization involving the central carbon atom of the cumulene system and the terminal hydroxyl group under basic catalytic conditions to form diethyl (4R)-[(4-hydroxy-4,5-dihydrofuran-2-yl)methyl]phosphonate (2) [1]. Phosphonate 2 is a highly reactive compound and is of interest as a structural unit for creating biologically active phosphonates.

Continuing a study related to the synthesis and chemical properties of phosphorylated heterocycles we have hydrogenated compound 2 with the aim of synthesizing the tetrahydrofuran derivative. However, it was found that hydrogenation caused opening of the 2,3-dihydrofuran ring. Using column chromatography we were able to isolate the main reaction product as the diethyl (5-hydroxy-2-oxopentyl)phosphonate ( 3).


dihydrofuran phosphoorganic compounds hydrogenation tautomerism 


  1. 1.
    V. K. Brel, Synthesis, 1539 (2001).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  1. 1.Institute of Physiologically Active SubstancesRussian Academy of SciencesChernogolovkaRussia

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