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Practical and convenient synthesis of coumarins from phenols and propiolic acid esters

Nature Protocols volume 2, pages 845–848 (2007)Cite this article

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Abstract

This protocol describes the synthesis of 6,7-methylenedioxy-4-phenylcoumarin from sesamol and ethyl phenylpropiolate using a Pd(OAc)2 catalyst to illustrate coumarin synthesis. This procedure is simple and easy and can be applied to the synthesis of other coumarins that have electron-rich phenol groups. The reaction is conducted by stirring a solution of Pd(OAc)2, sesamol and ethyl phenylpropiolate in trifluoroacetic acid at room temperature (15–20 °C) under atmospheric conditions. This protocol can be completed in 3 d.

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Figure 1: Scheme for hydroarylation of alkynes.
Figure 2: Scheme for synthesis of coumarins through intramolecular cyclization.
Figure 3: Scheme for synthesis of coumarins by a direct reaction of phenols and ethyl propiolates.
Figure 4: Scheme for synthesis of coumarin 3 catalyzed by Pd(OAc)2.

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Change history

  • 28 June 2007

    In the version of this article initially published online, the third author’s name appeared as Toshiyuki Tsubota instead of Toshiki Tsubota. The name has been corrected in all versions of the article.

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Acknowledgements

This work was supported partially by a grant-in-aid for scientific research on priority areas, 'Advanced Molecular Transformations of Carbon Resources', from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

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Authors and Affiliations

  1. Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi, 840-8502, Saga, Japan

    Tsugio Kitamura & Juzo Oyamada

  2. Department of Materials Science, Faculty of Engineering, Kyushu Institute of Technology, Sensui-cho, Tobata-ku, 804-8502, Kitakyushu, Japan

    Toshiki Tsubota

Authors
  1. Tsugio Kitamura
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  2. Juzo Oyamada
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  3. Toshiki Tsubota
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Correspondence to Toshiki Tsubota.

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Kitamura, T., Oyamada, J. & Tsubota, T. Practical and convenient synthesis of coumarins from phenols and propiolic acid esters. Nat Protoc 2, 845–848 (2007). https://doi.org/10.1038/nprot.2007.103

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