Mild and efficient solvent-free tetrahydropyranylation (THP) of alcohols catalyzed by reusable acidic ionic liquid [Et3N(CH2)4SO3H][OTs]

Document Type: Articles

Authors

1 Department of Pharmacology, University of Wisconsin Med. Sch., 1300 University Avenue, Madison, WI 53706-1532, USA Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran.

2 Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran.

Abstract

A variety of alcohols readily add to 3,4-dihydro-2H-pyran under solvent free conditions in the presence of catalytic amount of acidic ionic liquid [Et3N(CH2)4SO3H][OTs] to afford the corresponding tetrahydropyranyl ethers in good to excellent yields at room temperature. The use of this procedure allows easy separation of the desired products from ionic liquid and recycling the ionic liquid. Some of the major advantages of this procedure are nonaqueous work-up, very good yields, catalytic amount of catalyst and reusability of ionic liquid.

Keywords


[1] M. Bodanszky, Y.S. Klausner, M.A. Ondetti, Peptide synthesis, Wiley, 1976.
[2] J.H. van Boom, P.M.J. Burgers, G.R. Owen, C.B. Reese, R. Saffhill, J. Chem. Soc. Chem. Commun. (1971) 869-871.
[3] C. Augé, C.D. Warren, R.W. Jeanloz, M. Kiso, L. Anderson, Carbohydrate Res. 82 (1980) 85-95.
[4] R. Tschesche, Angew. Chem. 77 (1965) 184-184.
[5] P.G.M. Wuts, T.W. Greene, Greene's Protective Groups in Organic Synthesis, Wiley, 2006.
[6] M. Miyashita, A. Yoshikoshi, P.A. Grieco, J. Org. Chem. 42 (1977) 3772-3774.
[7] R.D. Johnston, C.R. Marston, P.E. Krieger, G.L. Goe, Synthesis (1988) 393-394.
[8] G.A. Olah, A. Husain, B.P. Singh, Synthesis (1985) 703-704.
[9] V. Bolitt, C. Mioskowski, D.S. Shin, J. Falck, Tetrahedron Lett. 29 (1988) 4583-4586.
[10] S. Hoyer, P. Laszlo, M. Orlović, E. Polla, Synthesis (1986) 655-657.
[11] Y. Morizawa, I. Mori, T. Hiyama, H. Nozaki, Synthesis (1981) 899-901.
[12] G.A. Olah, A. Husain, B.P. Singh, Synthesis (1983) 892-895.
[13] J. Yadav, D. Srinivas, G.S. Reddy, Synth. Commun. 28 (1998) 1399-1404.
[14] N. Deka, J.C. Sarma, Synth. Commun. 30 (2000) 4435-4441.
[15] N. Rezai, F.A. Meybodi, P. Salehi, Synth. Commun. 30 (2000) 1799-1805.
[16] S. Naik, R. Gopinath, B.K. Patel, Tetrahedron Lett. 42 (2001) 7679-7681.
[17] M.M. Heravi, F.K. Behbahani, H.A. Oskooie, R. Hekmat Shoar, Tetrahedron Lett. 46 (2005) 2543-2545.
[18] M.H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, V. Mirkhani, B. Yadollahi, Tetrahedron Lett. 42 (2001) 2851-2853.
[19] Y.G. Wang, X.X. Wu, Z.Y. Jiang, Tetrahedron Lett. 45 (2004) 2973-2976.
[20] A.T. Khan, S. Ghosh, L.H. Choudhury, Eur. J. Org. Chem. 2005 (2005) 4891-4896.
[21] S. Islam, A. Majee, A. Khan, Synth. Commun. 35 (2005) 1789-1793.
[22] T.S. Reddy, K. Ravinder, N. Suryakiran, M. Narasimhulu, K.C. Mahesh, Y. Venkateswarlu, Tetrahedron Lett. 47 (2006) 2341-2344.
[23] A.R. Hajipour, G. Azizi, A.E. Ruoho, Synlett (2009) 1974-1978.
[24] B.P. Bandgar, V.S. Sadavarte, L.S. Uppalla, S.V. Patil, Monatsh. Chem. 134 (2003) 425-428.
[25] A. Khazaei, A. Rostami, M. Mahboubifar, Catal. Commun. 8 (2007) 383-388.
[26] T. Mineno, Tetrahedron Lett. 43 (2002) 7975-7978.
[27] Y.-S. Hon, C.F. Lee, Tetrahedron Lett. 40 (1999) 2389-2392.
[28] B. Tamami, K. Parvanak Borujeny, Tetrahedron Lett. 45 (2004) 715-718.
[29] A.T. Khan, L.H. Choudhury, S. Ghosh, Tetrahedron Lett. 45 (2004) 7891-7894.
[30] G.P. Romanelli, G. Baronetti, H.J. Thomas, J.C. Autino, Tetrahedron Lett. 43 (2002) 7589-7591.
[31] S. Palaniappan, M. Sai Ram, C.A. Amarnath, Green Chem. 4 (2002) 369-371.
[32] L.C. Branco, C.A. Afonso, Tetrahedron 57 (2001) 4405-4410.
[33] B. Karimi, J. Maleki, Tetrahedron Lett. 43 (2002) 5353-5355.
[34] V.V. Namboodiri, R.S. Varma, Chem. Commun. (2002) 342-343.
[35] B. Choudary, V. Neeraja, M. Lakshmi Kantam, J. Mol. Catal. A: Chem. 175 (2001) 169-172.