Citation: Wang Jingjing, Zhao Xinyu, He Ming, Lv Yingtao, Kang Congmin. Improved Synthesis of Ethyl Benzofuran-3-Carboxylate[J]. Chemistry, ;2019, 82(1): 92-95. shu

Improved Synthesis of Ethyl Benzofuran-3-Carboxylate

1.
College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042
2.
College of Marine Science and Biological Engineering, Qingdao University of Science and Technology, Qingdao 266042

Corresponding author: Kang Congmin, lvyingao@qu.edu.cn
Received Date: 31 May 2018
Accepted Date: 2 September 2018

The benzofuran skeleton widely exists in natural products and synthetic medicines. Many benzofuran derivatives have important physiological, pharmacological and toxicological activities, and their synthesis methods have attracted much attention. A method of "one pot" synthesis ethyl benzofuran-3-carboxylate was obtained:in the presence of Et₃N, toluene was used as a solvent, the mole ratio of o-iodophenol to ethyl propiolate was 1:1.5, and the reaction was carried out at room temperature for 20 min; then adding K₂CO₃, Pd(OAc)₂/PPh₃ 85℃ for 3.5h, the product yield reached 78%. By improving the synthesis method, the process avoids the use of highly toxic diazo compound, and has the advantages of less steps, short time, simple operation and high yield. The method reported in this paper has implications for the synthesis of similar compounds.
- o-Iodophenol,
- Ethyl propiolate ethyl,
- Ethyl benzofuran-3-carboxylate,
- One pot synthesis
1. [1]
  K Asoh, M Kohchi, I Hyoudoh et al. Bioorg. Med. Chem. Lett., 2009, 19(6): 1753~1757.
2. [2]
  K A Reddy, B B Lohray, V Bhushan et al. J. Med. Chem., 1999, 42(11): 1927~1940.
3. [3]
  I Hayakawa, R Shioya, T Agatsuma et al. Bioorg. Med. Chem. Lett., 2004, 14(13): 3411~3414.
4. [4]
  M Ohno, M Miyamoto, K Hoshi et al. J. Med. Chem., 2005, 48(16): 5279~5294.
5. [5]
  M Thevenin, S Thoret, P Grellier et al. Bioorg. Med. Chem., 2013, 21(17): 4885~4892.
6. [6]
  M Koca, S Servi, C Kirilmis et al. Eur. J. Med. Chem., 2005, 40(12): 1351~1358.
7. [7]
  M Saleeb, S Mojica, A U Eriksson et al. Eur. J. Med. Chem., 2018, 143: 1077~1089.
8. [8]
  H Khanam, Shamsuzzaman. Eur. J. Med. Chem., 2015, 97: 483~504.
9. [9]
  F Karatas, M Koca, H Kara et al. Eur. J. Med. Chem., 2006, 41(5): 664~669.
10. [10]
  X Fang, R Z Heng, X Z Hao et al. Eur. J. Med. Chem., 2015, 89: 310~319.
11. [11]
  T Vang, Y Xie, W H Liu et al. J. Med. Chem., 2015, 54(2): 562~571.
12. [12]
  S Rizzo, C Rivière, L Piazzi et al. J. Med. Chem., 2008, 51(10): 2883~2886.
13. [13]
  Z J Zhu, Y Zhao, J B Li et al. Mol. Carcinog., 2016, 55(10): 1399~1410.
14. [14]
  R B Teponno, S Kusari, M Spiteller. Nat. Prod. Rep., 2016, 33(9): 1044~1092.
15. [15]
  Y Chen, S Chen, X Lu et al. Bioorg. Med. Chem. Lett., 2009, 19(7): 1851~1854.
16. [16]
  M Dixit, B K Tripathi, A K Tamrakar et al. Bioorg. Med. Chem., 2007, 15(2): 727~734.
17. [17]
  O Oter, K Ertekin, C Kirilmis et al. Sens. Actuat. B, 2007, 122(2): 450~456.
18. [18]
  Z Tomaszewski, M P Johnson, X Huang et al. J. Med. Chem., 1992, 35(11): 2061~2064.
19. [19]
  L Qin, D D Vo, A Nakhai, C D Andersson et al. ACS Comb. Sci., 2017, 19(6): 370~376.
20. [20]
  S M Gomha, A O Abdelhamid, N A Abdelrehem et al. J. Heterocycl. Chem., 2018, 55(4): 995~1001.
21. [21]
  M Hranjec, I Sovic, I Ratkaj et al. Eur. J. Med. Chem., 2013, 59: 111~119.
22. [22]
  R Chinchilla, C Najera. Chem. Rev., 2014, 114(3): 1783~826.
23. [23]
  C L Li, Y C Zhang, P H Li et al. J. Org. Chem., 2011, 76(11): 4692~4696.
24. [24]
  J A Malona, J M Colbourne, A J Frontier. Org. Lett., 2006, 8(24): 5661~5664.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142