A Convenient Method of Synthesizing 3-Ethoxycarbonylbenzofurans from Salicylaldehydes and Ethyl Diazoacetate

Abstract

We have developed a convenient one-pot procedure for the synthesis of 3-ethoxycarbonylbenzofurans from commercially available salicylaldehydes and ethyl diazoacetate. The method is high-yielding, efficient, simple and selective.

benzofurans - salicylaldehyde - ethyl diazoacetate

References

1a The Chemistry of Heterocyclic Compounds: Benzofurans   Weissberger A. Taylor EC. John Wiley and Sons; New York: 1974.  Vol. 29: 

1b Boyle EA. Morgan FR. Markwell RE. Smith SA. Thomson MJ. Ward RW. Wyman PA. J. Med. Chem.  1986,  29:  894 

1c Pieters L. Van Dyck S. Gao M. Bai R. Hamel E. Vlietinck A. Lemiere G. J. Med. Chem.  1999,  42:  5475 

1d Ma C.-Y. Liu WK. Che C.-T. J. Nat. Prod.  2002,  65:  206 

1e Baxendale IR. Griffiths-Jones CM. Ley SV. Tranmer GK. Synlett  2006,  427 

2a Liao Y. Reitman M. Zhang Y. Fathi R. Yang Z. Org. Lett.  2002,  4:  2607 

2b Willis MC. Taylor D. Gillmore AT. Org. Lett.  2004,  6:  4755 

2c Lu K. Luo T. Xiang Z. You Z. Fathi R. Chen J. Yang Z. J. Comb. Chem.  2005,  7:  958 

2d Nan Y. Miao H. Yang Z. Org. Lett.  2000,  2:  297 

3 Oftedahl ML. Baker JW. Dietrich MW. J. Org. Chem.  1965,  30:  296 

4 Dudley ME. Morshed MM. Brennan CL. Islam MS. Ahmad MS. Atuu MR. Branstetter B. Hossain MM. J. Org. Chem.  2004,  69:  7599 

5 Rabjohn N. Org. Synth. Coll. Vol. IV   John Wiley and Sons; New York: 1963.  p.424