Synlett 2013; 24(6): 737-740
DOI: 10.1055/s-0032-1318347
letter
© Georg Thieme Verlag Stuttgart · New York

CuBr2-Promoted Tetrahydrofuranylation of Alcohols and 1,3-Dione

Meng-Ke Wang
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Fax: +86(577)86689300   Email: dengchenliang78@tom.com
,
Zeng-le Zhou
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Fax: +86(577)86689300   Email: dengchenliang78@tom.com
,
Ri-Yuan Tang
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Fax: +86(577)86689300   Email: dengchenliang78@tom.com
,
Xing-Guo Zhang
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Fax: +86(577)86689300   Email: dengchenliang78@tom.com
,
Chen-liang Deng*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Fax: +86(577)86689300   Email: dengchenliang78@tom.com
› Author Affiliations
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

 
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  • 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).