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Synthesis, X-ray structure determination and analysis of packing interactions in 9-(1,2-propenyl)-6-carboethoxy-2-methyl-2,3-dihydrofuro[2,3-h]-benzopyran-5H-one

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Abstract

Claisen rearrangement of ethyl-2,4-diallyloxy-α-carbethoxycinnamate (1) in refluxing DMA afforded ethyl-9-allyl-2-methyl-2,3-dihydrofuro(2,3-h)benzopyran-5H-one-6-carboxylate (2) in a single step. Dehydrogenation with Pd/C (10%) in DPE furnished an unexpected isomeric compound, 9-(1,2-propenyl)-6-carbethoxy-2-methyl-2,3-dihydrofuro[2,3-h]-benzopyran-5H-one (3). This compound, C18H18O5, crystallizes in the monoclinic space group P21/n with unit cell parameters, a = 7.346(1), b = 16.482(3), c = 12.653(2),Å, and β = 92.71(1)°. The structure has been solved by direct methods and refined to R = 0.056 for 1719 observed reflections. The coumarin nucleus is planar. The five-membered ring is in envelope-conformation. The crystal structure is stabilized by intra- and intermolecular C―H⋯O hydrogen bonds.

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Authors and Affiliations

  1. Condensed Matter Physics Group, Department of Physics, University of Jammu, Jammu Tawi, 180006, India

    Rajnikant, Vivek K. Gupta,  Dinesh & Rachna Gupta

  2. Chemistry Department, Faculty of Science, M.S. University of Baroda, Baroda, 390002, India

    Samir V. Mistry, Suresh M. Desai, S. S. Madhava Rao & Amrish C. Shah

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  1. Rajnikant
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  2. Vivek K. Gupta
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  3. Dinesh
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  4. Rachna Gupta
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Rajnikant, Gupta, V.K., Dinesh et al. Synthesis, X-ray structure determination and analysis of packing interactions in 9-(1,2-propenyl)-6-carboethoxy-2-methyl-2,3-dihydrofuro[2,3-h]-benzopyran-5H-one. J Chem Crystallogr 34, 735–741 (2004). https://doi.org/10.1007/s10870-004-7648-x

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  • DOI: https://doi.org/10.1007/s10870-004-7648-x

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