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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

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     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)
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