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(13): 1702-1706
DOI: 10.1055/s-0033-1339310
DOI: 10.1055/s-0033-1339310
letter
Antimony(V) Chloride as an Efficient Reagent for Deprotection of Methyl Ethers
Further Information
Publication History
Received: 21 May 2013
Accepted after revision: 29 May 2013
Publication Date:
16 July 2013 (online)
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.
-
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
- 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