Antimony(V) Chloride as an Efficient Reagent for Deprotection of Methyl Ethers

Fariba Saadati; Hamid Meftah-Booshehri

doi:10.1055/s-0033-1339310

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(13): 1702-1706
DOI: 10.1055/s-0033-1339310

letter

Antimony(V) Chloride as an Efficient Reagent for Deprotection of Methyl Ethers

Fariba Saadati*

Department of Chemistry, Faculty of Science, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran Fax: +98(241)2283203 eMail: saadati@znu.ac.ir

,

Hamid Meftah-Booshehri

Department of Chemistry, Faculty of Science, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran Fax: +98(241)2283203 eMail: saadati@znu.ac.ir

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

This paper proposes a new and efficient method for the deprotection of methyl ethers using antimony pentachloride at ambient temperature. The procedure described here is a facile and practical method for the removal of the methyl group from aryl and benzyl methyl ethers. High selectivity was observed for the removal of the methyl group from dimethoxyarenes. The notable advantages of this protocol are mild reaction conditions, high yields, and the facility of workup procedure. The mechanism of the ether cleavage is proposed to explain this new reaction.

Key words

demethylation - methyl ether - antimony pentachloride - selectivity - dimethoxyarenes

Volltext

Referenzen

References
1 Greene TW, Wuts PG. M. Protective Groups in Organic Synthesis . 3rd ed. Wiley; New York: 1999

2a Achiet D, Rochelle D, Murengezi I, Delmas M, Gaset A. Synthesis 1986; 642
2b Winters RT, Sercel AD, Showalter HD. H. Synthesis 1988; 712
2c Basak A, Nayak MK, Chakraborti AS. Tetrahedron Lett. 1998; 39: 4883

3a Johnstone RA. W, Rose ME. Tetrahedron 1979; 35: 2169
3b Lee JC, Yuk JY, Cho SH. Synth. Commun. 1995; 25: 1367

4 Ouk S, Thiébaud S, Borredon E, Gars PL. Green Chem. 2002; 4: 431

5a Wiberg KB, Saegebarth KA. J. Org. Chem. 1960; 25: 832
5b Maggioni P, Minisci F. UK 2085004, 1984 ; Chem. Abstr. 1984, 96, 180960

6a Mossman AB. US 4611084, 1986 ; Chem. Abstr. 1986, 105, 193360
6b Furusaki S, Matsuda M, Saito M, Shiomi Y, Nakamura Y, Tobita M. US 5189225, 1993 ; Chem. Abstr. 1993, 115, 49082.
6c Rajaram Bal R, Chaudhari K, Sivasanker S. Catal. Lett. 2000; 70: 75

7a Weissman SA, Zewge D. Tetrahedron 2005; 61: 7833
7b Srivastava A, Yang J, Zhao B, Jiang Y, Blackmon W, Kraemer B. Synth. Commun. 2010; 41: 1765
7c Kocienski PJ. Protecting Groups . Thieme; Stuttgart: 1994

8a Dodge JA, Stocksdale MG, Fahey KJ, Jones CD. J. Org. Chem. 1995; 60: 739
8b Ranu BC, Bhar S. Org. Prep. Proced. Int. 1996; 28: 371
8c Kale B, Shinde A, Sonar S, Shingate B, Kumar S, Ghosh S, Venugopal S, Shingare M. Tetrahedron Lett. 2010; 51: 3075

9 Snyder CD, Rapoport H. J. Am. Chem. Soc. 1972; 94: 227

10a Maercker A. Angew. Chem., Int. Ed. Engl. 1987; 26: 972
10b Coop A, Janetka JW, Lewis JW, Rice KC. J. Org. Chem. 1998; 63: 4392
10c Casado F, Pisano L, Farriol M, Gallardo I, Marquet J, Melloni G. J. Org. Chem. 2000; 65: 322

11a Olah GA, Husain A, Gupta BG. B, Narang SC. Angew. Chem. 1981; 93: 705
11b Ohsawa T, Hatano K, Kayoh K, Kotabe J, Oishi T. Tetrahedron Lett. 1992; 33: 5555
11c Azzena U, Denurra T, Melloni G, Fenude E, Rassu G. J. Org. Chem. 1992; 57: 1444
11d Shindo T, Fukuyama Y, Sugai T. Synthesis 2004; 692

12a Fang Z, Zhou GC, Zheng SL, He GL, Li JL, He L, Bei D. J. Mol. Catal. A: Chem. 2007; 274: 16
12b Fredriksson A, Stone-Elander S. J. Labelled Compd. Radiopharm. 2002; 45: 529

13a Stupperich E, Konle R, Eckerskorn C. Biochem. Biophys. Res. Commun. 1996; 223: 770
13b Neumann A, Engelmann T, Schmitz R, Greiser Y, Orthaus A, Diekert G. Arch. Microbiol. 2004; 181: 245

14a McOmie JF. W, Watts ML, West DE. Tetrahedron 1968; 24: 2289
14b Punna S, Meunier S, Finn MG. Org. Lett. 2004; 6: 2777

15 Learmonth DA, Alves PC. Synth. Commun. 2002; 32: 641
16 Horie T, Shibata K, Yamashita K, Kawamura Y, Tsukayama M. Chem. Pharm. Bull. 1997; 45: 446
17 Sharghi H, Tamaddon F. Tetrahedron 1996; 52: 13623
18 Maeyama K, Kobayashi M, Yonezawa N. Synth. Commun. 2001; 31: 869
19 Wu Y.-Q, Limburg DC, Wilkinson DE, Vaal MJ, Hamilton GS. Tetrahedron Lett. 2000; 41: 2847
20 Kulkarni PP, Kadam AJ, Mane RB, Desai UV, Wadgaonkar PP. J. Chem. Res., Synop. 1999; 6: 394
21 Zuo L, Yao S, Wang W, Duan W. Tetrahedron Lett. 2008; 49: 4054
22 Gutmann V. Coord. Chem. Rev. 1976; 18: 225
23 Connelly NG, Geiger WE. Chem. Rev. 1996; 96: 877
24 Glória PM. C, Prabhakar S, Lobo AM, Gomes MJ. S. Tetrahedron Lett. 2003; 44: 8819
25 Srinivas G, Periasamy M. Tetrahedron Lett. 2002; 43: 2785
26 Brüzga P, Grazulevičius JV, Kavaliünas R. Eur. Polym. J. 1991; 27: 707
27 Walker MA, Heathcock CH. J. Org. Chem. 1991; 56: 5747
28 Bigdeli MA, Rahmati A, Abbasi-Ghadim H, Mahdavinia GH. Tetrahedron Lett. 2007; 48: 4575
29 Muathen HA. Helv. Chim. Acta 2003; 86: 164

30a Brunel JM. Chem. Rev. 2005; 105: 857
30b Pandey SK. Synlett 2006; 3366

31a Uozumi Y, Tanahashi A, Lee SY, Hayashi T. J. Org. Chem. 1993; 58: 1945
31b Takahashi M, Ogasawara K. Tetrahedron: Asymmetry 1997; 8: 3125
31c Nakamura S, Kaneeda M, Ishihara K, Yamamoto H. J. Am. Chem. Soc. 2000; 122: 8120

32a Aldrich Catalog Handbook of Fine Chemicals 1996–1997. Milwaukee WI: 1996
32b Beilstein FK. Beilstein Handbuch der Organischen Chemie . 4th Suppl., Vol. 19 Springer; Berlin: 1972
32c Bayston DJ, Fraser JL, Ashton MR, Baxter AD, Polywka ME. C, Moses E. J. Org. Chem. 1998; 63: 3137