Methane-diphosphonic Acid Tetraethyl Ester.pdf

Molecules 2000, 5, M131

Methane-diphosphonic Acid Tetraethyl Ester

Didier Villemin

a

and Frédéric Thibault

b

ISMRA, 6 boulevard Maréchal Juin, F-14050 Caen, France; a) UMR 6507 CNRS, E-mail: Didier.Villemin@ismra.fr b) UMR

6506 CNRS

Received: 16 December 1999 / Accepted: 17 January 2000 / Published: 24 January 2000

Keywords: phosphonate, bioactive compound, material, alkene precursor.

Methanediphosphonic acid tetraethyl ester is a useful intermedaite for the synthesis of phosphonoalkenes

A solution of of sodium ethoxide was prepared by adding sodium metal (3 mol, 69 g) in portions to

absolute ethanol (900 ml). Diethyl phosphite (3 mol, 386ml) was added with stirring, and the mixture

stirred for 1h at ambient temperature. The excess of alcohol was evaporated using a rotary evaporator.

Dichloromethane (1000 ml) was added, and the mixture was agitated for 2 months in a closed bottle. The

mixture was washed with water (500 ml) and the organic phase was dried over magnesium sulfate. The

solvent was evaporated, and the product was obtained as a colourless liquid (89% yield) by distillation

[Bp : 128 °C(0.02)].

RN : 1660-94-2

1

H NMR (CCl

): 1.35 (t, J = 7 Hz, 12 H, P-O-C-CH

) 2.45 (t, J = 21 Hz, 2 H, P-CH

31

P NMR (CDCl

3

): 19.05.

IR (film) : 1250 (P=O), 1020 (P-O-C), 960, 820.

References

1. Cardogan, J. I. G. In Organophosphorus reagents in Organic Synthesis, Academic Press, London,

New York, 1979. Johnson A. In Ylid Chemistry, Academic Press, New York, 1966. Wadsworth,W. S.,

Jr. Organic Reaction 1978, 25, 73. Villieras, J.; Rambaud, M.; Kirschleger, B. Phosphorous and

Sulfur, 1983, 14, 385. Villieras, J.; Rambaud, M. Synthesis, 1982, 924 and 1983, 300. Villieras, J.;

Rambaud, M.; Graff, M. Tetrahedron Lett., 1985, 26, 53; Villemin, D.; Puciova-Sebova, M.; Toma, S.;

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