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Vinyl Ethers Containing an Epoxy Group: XXI. Synthesis and Acid-Catalyzed Cyclization of 1-[ω-(Vinyloxy)alkoxy]-3-(2-propynyloxy)-2-propanols- A Simple Route to 2-Propynyloxymethyl-Substituted Cyclic Polyethers

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Abstract

Base-catalyzed reaction of 2-[ω-(vinyloxy)alkoxy]methyloxiranes with 2-propynyl alcohol (∼3 wt % of t-BuOK, 60-85°C, 3-12 h) afforded first reperesentatives of the 1-[ω-(vinyloxy)alkoxy]-3-(2-propynyloxy)-2-propanol series in up to 99% yield. Treatment of 1-[2-(vinyloxy)ethoxy]- and 1-[2-(vinyloxy)ethoxyethoxy]-3-(2-propynyloxy)-2-propanols with trifluoroacetic acid (∼0.5 wt. %) in dry diethyl ether resulted in cyclization with formation of up to 96% of (2-methyl-1,3,6-trioxocan-4-yl)methyl- and (2-methyl-1,3,6,9-tetraoxacycloundecan-4-yl)methyl 2-propynyl ethers.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    L. P. Nikitina, L. L. Dmitrieva, A. I. Albanov & N. A. Nedolya

  2. Utrecht University, Utrecht, The Netherlands

    L. Brandsma

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  1. L. P. Nikitina
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  2. L. L. Dmitrieva
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  3. A. I. Albanov
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  4. N. A. Nedolya
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  5. L. Brandsma
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Nikitina, L.P., Dmitrieva, L.L., Albanov, A.I. et al. Vinyl Ethers Containing an Epoxy Group: XXI. Synthesis and Acid-Catalyzed Cyclization of 1-[ω-(Vinyloxy)alkoxy]-3-(2-propynyloxy)-2-propanols- A Simple Route to 2-Propynyloxymethyl-Substituted Cyclic Polyethers. Russian Journal of Organic Chemistry 39, 1384–1392 (2003). https://doi.org/10.1023/B:RUJO.0000010551.79215.53

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