Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 13
171
Views
21
CrossRef citations to date
0
Altmetric
Original Articles

On A Safe and Practical Method for The Preparation of β-Keto Phosphonates1

, &
Pages 2561-2568 | Received 15 Jan 1996, Published online: 23 Aug 2006

References

  • Presented in part at SFC 94, Congress of the «Société Française de Chimie», Lyon (France), September 1994
  • Homer , L. , Hoffman , H. , Wippell , H. G. and Klahre , G. 1959 . Chem. Ber. , 92 : 2499
  • Wadsworth , W. S. Jr. and Emmons , W. D. 1961 . J. Am. Chem. Soc. , 83 : 1733
  • Wadsworth , W. S. Jr. 1977 . Org. React. , 25 : 73
  • Walker , B. J. 1979 . Organophosphorus Reagents in Organic Synthesis , Edited by: Cadogan , J. L.G. 155 – 205 . London : Acad. Press .
  • Maryanoff , B. E. and Reitz , A. B. 1989 . Chem. Rev. , 89 : 863 and references therein
  • Cotton , F. A. and Schunn , R. A. 1963 . J. Am. Chem. Soc. , 85 : 2394
  • Youinou , M. T. , Guerchais , J. E. and Sturtz , G. 1973 . J. Mol. Struct. , 18 : 109
  • Martin , J. L. and Leroy , M. J. 1978 . J. Chem. Res. (S) , : 88
  • Sturtz , G. , Clément , J. C. , Daniel , A. , Molinier , J. and Lenzi , M. 1981 . Bull. Soc. Chim. Fr. , : 167
  • McCabe , D. J. , Duesler , E. N. and Paine , R. T. 1985 . Inorg. Chem. , 24 : 4626 and quoted references
  • Arbuzov , B. A. 1964 . Pure Appl. Chem. , 9 : 307
  • Corey , E. J. and Kwiatkowski , G. T. 1966 . J. Am. Chem. Soc. , 88 : 5654
  • Mathey , F. and Savignac , P. 1978 . Tetrahedron , 34 : 649
  • Nicolaou , K. C. , Seitz , S. P. , Pavia , M. R. and Petasis , N. A. 1979 . J. Org. Chem. , 44 : 4010
  • Mikolajczyk , M. and Balczewski , P. 1984 . Synthesis , : 691
  • Theisen , P. D. and Heathcock , C. H. 1988 . J. Org. Chem. , 53 : 2374
  • Koskinen , A. M.P. and Krische , M J . 1990 . Synlett , : 665
  • Chakravarty , P. K. , Combs , P. , Roth , A. and Greenlee , W. J. 1987 . Tetrahedon Lett. , 28 : 611
  • Coutrot , P. and Ghribi , A. 1986 . Synthesis , : 661
  • Grieco , P. A. and Pogonowski , C. S. 1973 . J. Am. Chem. Soc. , 95 : 3071
  • Delamarche , I. and Mosset , P. 1994 . J. Org. Chem. , 59 : 5453
  • Wenkert , E. and Schorp , M. K. 1994 . J. Org. Chem. , 59 : 1943
  • Perkow , W. , Ullerich , K. and Meyer , F. 1952 . Naturwissenschaften , 39 : 303
  • Borowitz , I. J. , Anschel , M. and Firstenberg , S. 1967 . J. Org. Chem. , 32 : 1723
  • Bianchini , J. P. and Gaydou , E. M. 1975 . C. R. Acad. Sci. Paris , 280 : 1521
  • Sturtz , G. 1964 . Bull. Soc. Chim. Fr. , : 2333
  • Corbel , B. , Medinger , L. , Haelters , J. P. and Sturtz , G. 1985 . Synthesis , : 1048 (methoxycarbonylhydrazones)
  • Yuan , C. and Xie , R. 1994 . Phosphorus, Sulf. and Sil. , 90 : 47 (benzenesulfonylhydrazones)
  • Sturtz , G. 1964 . Bull. Soc. Chim. Fr. , : 2340 (enols)
  • Sturtz , G. 1967 . Bull. Soc. Chim. Fr. , : 1345 (enamines)
  • Boeckman , R. K. , Walters , M. A. and Koyano , H. 1989 . Tetrahedron Lett. , 30 : 4787 (enamines)
  • Lee , K. and Oh , D. Y. 1991 . Synth. Commun. , 21 : 279 (enamines)
  • Sturtz , G. , Charrier , C. and Normant , H. 1967 . Bull. Soc. Chim. Fr. , : 1707 (acetylenic)
  • Chattha , M. S. and Aguiar , A. M. 1973 . J. Org. Chem. , 38 : 2908 (acetylenic)
  • Sturtz , G. and Pondaven-Raphalen , A. 1980 . Chem. Res. (M.) , : 2510 (ene derivatives)
  • Kim , D. Y. , Lee , K. and Oh , D. Y. 1992 . J. Chem. Soc. Perkin Trans , 1 : 2451 (nitronates)
  • Gasteiger , J. and Herzig , C. 1980 . Tetrahedron Lett. , 21 : 2687 (α-choroepoxides)
  • Krapcho , A. P. 1982 . Synthesis , : 805 and 893
  • Kim , D. Y. , Kong , M. S. and Rhie , D. Y. 1995 . Synth. Commun. , 25 : 2865
  • Walker , H. G. and Hauser , C. R. 1946 . J. Am. Chem. Soc. , 68 : 1386 and
  • Reynolds , G. A. and Hauser , C. R. 1963 . Org. Synth. Coll. , Vol. IV , 708 New York, N.Y. : J. Wiley ed. .
  • Bottin-Strzalko , T. , Corset , J. , Froment , F. , Pouet , M. J. , Seyden-Penne , J. and Simonnin , M. P. 1980 . J. Org. Chem. , 45 : 1270
  • Bottin-Strzalko , T. , Seyden-Penne , J. , Froment , F. , Corset , J. and Simonnin , M. P. 1988 . Can. J. Chem. , 66 : 391
  • Hanford , W. E. and Sauer , J. C. 1964 . Org. Reactions , 3 : 108
  • Kreutzkamp , N. 1955 . Chem. Ber. , 88 : 195
  • Durrant , G. and Sutherland , J. K. 1972 . J. Chem. Soc., Perkin I , : 2582 Addition of hexanoylchloride to the corresponding sodium enolate was reported to give the β-keto ester in 25% yield. See
  • Natchev , I. A. 1988 . Tetrahedron , 44 : 6455 For acylation of lithium enolate see
  • Rathke , M. W. and Cowan , P. J. 1985 . J. Org. Chem. , 50 : 2622
  • Kuo , D. L. 1992 . Tetrahedron , 48 : 9233
  • The magnesium ethoxide procedure to make 4 is an adaptation of the C.R. Hauser's method11. A few minutes after benzoyl chloride was added, 31P NMR analysis showed a 100% aroylation reaction. When propanoyl chloride was used 30 to 50% starting material were left. But, the successive additions of 0.5 eq. of magnesium ethoxide (Aldrich) and acyl chloride eventually led to the complete transformation of the starting material. (R' = C2H5, 80% yield; R' = Ph, 75% yield after distillation)
  • To the magnesium bromide-ether complex, made by reacting Br2 and magnesium turnings in ether, are added successively trialkyl phosphonoacetates 1 (1 eq.) in CH2Cl2 followed by triethylamine (2 eq.). After 30 minutes the acylating agent (1.1 eq.) is added dropwise. The resulting solution is checked by 31P NMR and worked up as described before. (R' = C2H5, 85% yield; R' = Ph, 75% yield after distillation)
  • Staab , H. A. 1962 . Angew Chem. , 74 : 407

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.