A Practical Synthesis of Diethyl 1-Methylthio-2-oxo-2-phenylethylphos­phonates from Diethyl Methylthiomethylphosphonate

Abstract

An efficient synthesis of 2′- and 3′-substituted diethyl 1-methylthio-2-oxo-2-phenylethylphosphonates 3a-k from 2′- and 3′-substituted benzoyl chlorides 2a-k using diethyl methylthio-1-lithiomethylphosphonate is described.

diethyl 1-methylthio-2-oxo-2-phenylethylphosphonates - diethyl methylthiomethylphosphonate - Michaelis-Arbuzov reaction - acylation reaction

References

1a Wadsworth WS. Emmons WD. J. Am. Chem. Soc.  1961,  83:  1733 

1b Horner L. Ertel H. Hoffmann H. Toscano VG. Klink W. Chem. Ber.  1962,  95:  581 

2 Isolani PC. Olivato PR. Ruiz Filho R. Vicentini G. Zukerman-Schpector J. J. Coord. Chem.  1999,  48:  391 

3 Michaelis A. Kaehne R. Ber. Dtsch. Chem. Ges.  1898,  31:  1048 

4 Bhattacharya AK. Thyagarajan G. Chem. Rev.  1981,  81:  415 

5 Lichtenthaler FW. Chem. Rev.  1961,  61:  607 

6a Chattha MS. Aguiar AM. J. Org. Chem.  1973,  38:  2908 

6b Gasteiger J. Herzig C. Tetrahedron Lett.  1980,  21:  2687 

6c Sturtz G. Corbel B. Medinger L. Haelthers JP. Sturtz G. Synthesis  1985,  1048 

6d Kim DY. Kong MS. J. Chem. Soc., Perkin Trans 1  1994,  3359 

7a Corey EJ. Kwiatkowski GT. J. Am. Chem. Soc.  1966,  88:  5654 

7b Mikolajczyk M. Balczewski P. Synthesis  1984,  691 

7c Aboujaoude EE. Collignon N. Savignac P. J. Organometal. Chem.  1984,  264:  9 

7d Aboujaoude EE. Collignon N. Teulade M.-P. Savignac P. Phosphorus and Sulfur  1985,  25:  57 

8 Hong SK. Chang KH. Ku BC. Oh DY. Tetrahedron Lett.  1989,  30:  3307 

9 Boeckman RK. Walters MA. Koyano H. Tetrahedron Lett.  1989,  30:  4787 

10 Mathey F. Savignac P. Tetrahedron  1978,  34:  649 

11a Kabat MM. Tetrahedron Lett.  1993,  34:  8543 

11b Altenbach HJ. Korff R. Tetrahedron Lett.  1981,  22:  5175 

12 Ohler E. Kang HS. Zbiral E. Synthesis  1988,  623 

13 Koh YJ. Oh DY. Tetrahedron Lett.  1993,  34:  2147 

14 Nicolaou KC. Seitz SP. Pavia MR. Petasis NA. J. Org. Chem.  1979,  44:  4011 

15 Kim DY. Mang JY. Oh DY. Synth. Commun.  1994,  24:  629 

16 Kim DY. Kong MS. Lee KS. J. Chem. Soc., Perkin Trans. 1  1997,  1361 

17a Kim DY. Kong MS. Rhie DY. Synth. Commun.  1995,  25:  2865 

17b Kim DY. Kong MS. Kim TH. Synth. Commun.  1996,  26:  2487 

17c Corbel B. L’Hostis-Kervella I. Haelters JP. Synth. Commun.  1996,  26 :  2561 

17d Corbel B. L’Hostis-Kervella I. Haelters JP. Synth. Commun.  2000,  30:  609 

18 Orsini F. Di Teodoro E. Ferrari M. Synthesis  2002,  1683 

19 Coutrot P. Ghribi A. Synthesis  1986,  661 

20 Rodrigues A. Ph.D. Thesis   Universidade de São Paulo; Brazil: 2003. 

21

These reactions are in progress in our laboratory.

22 Bordwell FG. Pitt BM. J. Am. Chem. Soc.  1955,  77:  572 

23 Kreutzkamp N. Pluhatsch J. Arch. Pharm. (Weinheim, Ger.)   292:  1959.  p.159 

24 Harpp DN. Bao LC. Black CJ. Gleason JG. Smith RA. J. Org. Chem.  1975,  40:  3420