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Synlett 2012; 23(17): 2473-2476
DOI: 10.1055/s-0032-1317195
letter
© Georg Thieme Verlag Stuttgart · New York

Amberlyst-15-Catalyzed One-Pot Synthesis of 2-Aryltetrahydrofurans from Tetrahydrofuran

Hande Gunduz
Department of Chemistry, Istanbul Technical University, Maslak, 34469 Istanbul, Turkey   Fax: +90(212)2856386   Email: talinlin@itu.edu.tr
,
Volkan Kumbaraci
Department of Chemistry, Istanbul Technical University, Maslak, 34469 Istanbul, Turkey   Fax: +90(212)2856386   Email: talinlin@itu.edu.tr
,
Naciye Talinli*
Department of Chemistry, Istanbul Technical University, Maslak, 34469 Istanbul, Turkey   Fax: +90(212)2856386   Email: talinlin@itu.edu.tr
› Author Affiliations
Further Information

Publication History

Received: 14 July 2012

Accepted after revision: 14 August 2012

Publication Date:
21 September 2012 (online)

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Abstract

A simple one-step route for the conversion of naphthols and phenols with tetrahydrofuran into corresponding 2-aryltetrahydrofurans using Amberlyst-15 as a catalyst is reported. This is the first example of the acid-mediated formation and rearrangement reactions of tetrahydrofuranyl ethers prepared from the tetrahydrofuran and aromatic/aliphatic hydroxy compounds.

Key words

2-aryltetrahydrofurans - tetrahydrofuranyl ethers - Amberlyst-15 - rearrangement reactions - naphthols

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

  • 1 Williams GB. D, Simelane SB, Lawton M, Kinfe HH. Tetrahedron 2010; 66: 4573
    CrossrefSearch in Google Scholar
  • 2 Katsuki T, Nagano H. Chem. Lett. 2002; 722105
  • 3 Kometani T, Kondo H, Fujimori Y. Synthesis 1988; 1005
    Thieme Connect
  • 4 Baati R, Valleix A, Mioskowski C, Barma DK, Falck JR. Org. Lett. 2000; 2: 485
    CrossrefPubMedSearch in Google Scholar
  • 5 Barks JM, Gilbert BC, Parsons AF, Upeadran B. Tetrahedron Lett. 2000; 41: 6249
    CrossrefSearch in Google Scholar
  • 6 Falck JR, Li DR, Bejot R, Mioskowski C. Tetrahedron Lett. 2006; 47: 5111
    CrossrefSearch in Google Scholar
  • 7 Ochiai M, Sueda T. Tetrahedron Lett. 2004; 45: 3557
    CrossrefSearch in Google Scholar
  • 8 Das B, Krishnaiah M, Reddy VS, Laxminarayana K. Helv. Chim. Acta 2007; 90: 2163
    CrossrefSearch in Google Scholar
  • 9 Troisi L, Granito C, Rondizi L, Rosato F, Videtta V. Tetrahedron Lett. 2010; 51: 5980
    CrossrefSearch in Google Scholar
  • 10 Pinhey JT, Xuan PT. Aust. J. Chem. 1988; 41: 69
    CrossrefSearch in Google Scholar
  • 11 Talinli N, Karliga B. J. Heterocycl. Chem. 2004; 41: 205
    CrossrefSearch in Google Scholar
  • 12 General Procedure for Tetrahydrofuranylation of Aromatic and Aliphatic Hydroxy Compounds THF, aromatic or aliphatic hydroxy compounds, and Amberlyst-15 was stirred for 5–8 h. At the end of the reaction, the mixture was filtered to remove the Amberlyst-15 resins. The organic layer was dried over Na2SO4, filtered, and the solvent was evaporated under reduced pressure, and the products were purified by chromatographic methods. 1-(Tetrahydrofuran-2-yl)naphthalen-2-ol (1)
     1H NMR (300 MHz, CDCl3): δ = 9.75 (s, 1 H), 7.67–7.65(d, J = 8.1 Hz, 1 H), 7.64–7.58 (dd, J = 8.19, 3.2 Hz, 1 H), 7.36 (td, J = 7.2, 7.0, 1.0 Hz, 1 H), 7.36–7.34 (dd, J = 6.8, 1.0 Hz, 1 H), 7.34–7.32 (dd, J = 7.2, 1.1 Hz, 1 H), 7.11–7.08 (d, J = 8.8 Hz, 1 H), 5.73 (t, J = 6.5 Hz, 1 H), 4.21–4.28 (dd, J = 7.0, 8.3 Hz, 1 H), 3.94–3.86 (dd, J = 7.2, 8.4 Hz, 1 H), 2.56–2.50 (m, 1 H), 2.07–2.00 (m, 2 H), 1.85–1.80 (m, 1 H). 13C NMR (75 MHz, CDCl3): δ = 153.80, 131.70, 129.45, 128.96, 128.77, 126.61, 122.91, 121.49, 120.1, 114.75, 81.14, 68.71, 33.77, 25.92. IR (neat): 3240, 3053, 2946, 2879, 1623, 1467, 1262, 1041, 816 cm–1. MS (EI): m/z (%) = 213.8 (100) [M+], 182.8 (46), 164.8 (64), 152.9 (20), 114.8 (30), 62.9 (6). 2,4-Dimethyl-6-(tetrahydrofuran-2-yl)phenol (6)
     1H NMR (250 MHz, CDCl3): δ = 8.45 (br, s, 1 H), 6.91 (s, 1 H), 6.61 (s, 1 H), 4.93 (t, J = 8.4 Hz, 1 H), 4.10 (m, 1 H), 3.92 (m, 1 H), 2.27 (m, 2 H), 2.18 (s, 3 H), 2.01 (s, 3 H), 1.95 (m, 2 H). 13C NMR (75 MHz, CDCl3): δ = 151.36, 130.63, 130.02, 128.04, 124.91, 123.78, 82.45, 68.40, 33.17, 25.45, 20.45, 15.77. IR (neat): 3300, 2922, 2870, 1613, 1486, 1228, 1049 cm–1. MS (EI): m/z (%) = 191.9 (80) [M+], 160.9 (100), 159.0 (42), 146.0 (34), 91.0 (34), 77.0 (30), 41.0 (20).
  • 13 Salavati-Niasari M. Inorg. Chem. Commun. 2006; 628
  • 14 Liang G, Gannett P, Shi X, Zhang Y, Chen F, Gold B. J. Am. Chem. Soc. 1994; 116: 1131
    CrossrefSearch in Google Scholar
  • 15 Lawson AP, Klang JA. Synth. Commun. 1993; 23: 3205
    CrossrefSearch in Google Scholar
  • 16 Liu H, Wan S, Florencig PE. J. Org. Chem. 2005; 70: 3815
    Search in Google Scholar
  • 17 Kruse CG, Broekhof NL. J. M, Gen A. Tetrahedron Lett. 1976; 20: 1725
    Search in Google Scholar