Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2013; 24(6): 737-740
DOI: 10.1055/s-0032-1318347
DOI: 10.1055/s-0032-1318347
letter
CuBr2-Promoted Tetrahydrofuranylation of Alcohols and 1,3-Dione
Further Information
Publication History
Received: 07 January 2013
Accepted after revision: 11 February 2013
Publication Date:
06 March 2013 (online)
Abstract
A method for the CuBr2-promoted tetrahydrofuranylation of alcohols and 1,3-dione has been developed. A variety of different alcohols were efficiently converted into the corresponding 2-tetrahydrofuran ethers in the presence of CuBr2. It is noteworthy that this protocol also successfully converted 1,3-diphenyl-1,3-dione into the corresponding 2-tetrahydrofuran derivative in good yield.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Greene TW, Wuts PG. M. Protective Groups in Organic Chemistry . Wiley; New York: 1999. Chap. 2, 57-58
- 2a Miyashita M, Yoshikoshi A, Grieco PA. J. Org. Chem. 1977; 42: 3772
- 2b Bongini A, Cardillo G, Orena M, Sandri S. Synthesis 1979; 618
- 2c Morizawa Y, Mori I, Hiyama T, Nozaki H. Synthesis 1981; 899
- 2d Olah GA, Husain A, Singh BP. Synthesis 1985; 703
- 2e Bolitt V, Mioskowski C, Shin DS, Falck JR. Tetrahedron Lett. 1988; 29: 4583
- 2f Ranu BC, Saha M. J. Org. Chem. 1994; 59: 8269
- 2g Bhalerao UT, Davis KJ, Rao BV. Synth. Commun. 1996; 26: 3081
- 2h Habibi MH, Tangestaninejad S, Mohammadpoor-Baltork I, Mirkhani V, Yadollahi B. Tetrahedron Lett. 2001; 42: 2851
- 2i Stephens JR, Butler PL, Clow CH, Oswald MC, Smith RC, Mohan R. Eur. J. Org. Chem. 2003; 3827
- 3a Kruse CG, Broekhof NL. J. M, van der Gen A. Tetrahedron Lett. 1976; 1725
- 3b Kruse CG, Poels EK, Jonkers FL, van der Gen A. J. Org. Chem. 1978; 43: 3548
- 3c Yu B, Hui Y. Synth. Commun. 1995; 25: 2037
- 3d Hon YS, Lee CF. Tetrahedron Lett. 1999; 40: 2389
- 3e Barks JM, Gilbert BC, Parsons AF, Upeandran B. Tetrahedron Lett. 2000; 41: 6249
- 3f French AN, Cole J, Wirth T. Synlett 2004; 2291
- 4 Maione AM, Romeo A. Synthesis 1987; 250
- 5 Van Boom JH, Herschied JD. M, Reese CB. Synthesis 1973; 169
- 6 Baati R, Valleix A, Mioskowski C, Barma DK, Falk JR. Org. Lett. 2000; 2: 485
- 7 Masahito O, Takuya S. Tetrahedron Lett. 2004; 45: 3557
- 8 Jung JC, Choi HC, Kim YH. Tetrahedron Lett. 1993; 34: 3581
- 9 Falck JR, Li DR, Bejot R, Mioskowski C. Tetrahedron Lett. 2006; 47: 5111
- 10 Williams DB. G, Simelane SB, Lawton M, Kinfe HH. Tetrahedron 2010; 66: 4573
- 11 Troisi L, Granito C, Ronzini L, Rosato F, Videtta V. Tetrahedron Lett. 2010; 51: 5980
- 12 Typical Procedure: To a Schlenk tube were added phenylmethanol 1 (0.3 mmol), CuCl2 (10 mol%), and THF (2 mL). The tube was stirred at 100 °C (oil bath temperature) under an air atmosphere for the indicated time until complete consumption of starting material was monitored by TLC and GC-MS analyses. When the reaction was finished, the mixture was cooled to room temperature, diluted in diethyl ether, and washed with brine. The aqueous phase was re-extracted with diethyl ether and the combined organic extracts were dried over Na2SO4 and concentrated in vacuum, and the resulting residue was purified by silica gel column chromatography (hexane–EtOAc) to afford the target product 3. 2-(Benzyloxy)tetrahydrofuran (3): Colorless liquid. 1H NMR (300 MHz, CDCl3): δ = 7.36–7.27 (m, 5 H), 5.25–5.23 (m, 1 H), 4.73 (d, J = 12.0 Hz, 1 H), 4.49 (d, J = 12.0 Hz, 1 H), 4.01–3.88 (m, 2 H), 2.10–1.84 (m, 4 H). 13C NMR (125 MHz, CDCl3): δ = 138.4, 128.4, 127.85 (s), 127.5, 103.1, 68.8, 67.0, 32.4, 23.5. MS (EI, 70 eV): m/z (%) = 178 (2) [M]+, 91 (100), 71 (48), 108 (28), 92 (25).
For recent tetrahydropyranylations, see:
For recent tetrahydrofuranylations, see: