A New and More Efficient Synthesis
of Methylene Acetals

Guobiao Chu; Yanqiao Zhang; Chunbao Li; Yuqing Zhang

doi:10.1055/s-0029-1216992

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml

Teilen / Bookmarken

Facebook Linkedin Weibo

PDF herunterladen

Synthesis 2009(22): 3828-3832
DOI: 10.1055/s-0029-1216992

PAPER

A New and More Efficient Synthesis of Methylene Acetals

Guobiao Chu^a, Yanqiao Zhang^a, Chunbao Li*^a, Yuqing Zhang^b
^a Department of Chemistry, College of Science, Tianjin University, Tianjin 300072, P. R. of China
Fax: +86(22)27403475; e-Mail: lichunbao@tju.edu.cn;
^b School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. of China

Weitere Informationen

Publikationsverlauf

Received 18 June 2009
Publikationsdatum:
08. September 2009 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A new and efficient synthesis of benzyl chlorides and methylene acetals by use of 2,4-dichloro-6-methoxy[1,3,5]triazine (MeOTCT) and dimethyl sulfoxide has been developed. Chlorides are the major products for benzyl alcohols, while methylene acetals are the major products for secondary alcohols. This procedure provides the highest yields so far for methylene acetals of steroids. A plausible mechanism is proposed on the basis of the experiments.

Key words

2,4-dichloro-6-methoxy[1,3,5]triazine - dimethyl sulfoxide - alcohols - benzyl chlorides - methylene acetals

References

1a Williams AA. Lewis MJ. Tucknott OG. Food Chem. 1980, 6: 139

MissingFormLabel

Suche in Google Scholar
1b Bennett EO. Int. Biodeter. Bull. 1973, 9: 95

MissingFormLabel

Suche in Google Scholar
1c Dubois JL. inventors; Patent Application EP 1938684. ; Chem. Abstr. 2008, 149, 98879

MissingFormLabel
2 Greene TW. Wuts PG. Protective Groups in Organic Synthesis 3rd ed.: Wiley; Indianapolis: 1999. p.201

MissingFormLabel
Suche in Google Scholar
3 Goodwin JC. Hodge JE. Carbohydr. Res. 1973, 28: 213

MissingFormLabel
Crossref Suche in Google Scholar
4 Brimacombe JS. Foster AB. Jones BD. Willard JJ. J. Chem. Soc. C 1967, 2404

MissingFormLabel
Crossref
5 Guiso M. Procaccio C. Fizzano MR. Piccioni F. Tetrahedron Lett. 1997, 38: 4291

MissingFormLabel
Crossref Suche in Google Scholar
6a Hanessian S. Yang-Chung G. Lavallee P. Pernet AG. J. Am. Chem. Soc. 1972, 94: 8929

MissingFormLabel

Suche in Google Scholar
6b Munavu RM. J. Org. Chem. 1980, 45: 3341

MissingFormLabel

Suche in Google Scholar
7 Wang Q. Sun L. Jiang Y. Li C. Beilstein J. Org. Chem. 2008, 4: 51 ; DOI: 10.3762/bjoc.4.51

MissingFormLabel
PubMed Suche in Google Scholar
8a Blotny G. Tetrahedron 2006, 62: 9507

MissingFormLabel

Suche in Google Scholar
8b Das B. Venateswarlu K. Krishnaiah M. Helv. Chim. Acta 2007, 90: 149

MissingFormLabel

Suche in Google Scholar
8c Kunishima M. Yamamoto K. Hioki K. Kondo T. Hasegaua M. Tani S. Tetrahedron 2007, 63: 2604

MissingFormLabel

Suche in Google Scholar
8d Bigdeli MA. Heravi MM. Mahdavinia GH. Catal. Commun. 2007, 8: 1595

MissingFormLabel

Suche in Google Scholar
9 Sun L. Pei G. Niu H. Wang Q. Li C. Synthesis 2008, 3919

MissingFormLabel
Thieme Connect
10a Suzuki K. Inanaga J. Yamaguchi M. Chem. Lett. 1979, 1277

MissingFormLabel
10b Herz JE. Lucero J. Santoyo Y. Waight ES. Can. J. Chem. 1971, 49: 2418

MissingFormLabel

Suche in Google Scholar
10c Kaya IA. Jaret RS. J. Chem. Eng. Data 1971, 16: 485

MissingFormLabel

Suche in Google Scholar
10d Kupchan SM. Casy AF. Swintosky JW. J. Pharm. Sci. 1965, 54: 514

MissingFormLabel

Suche in Google Scholar
11 Wendt GR, and Ledig KW. inventors; US Patent 3267120. ; Chem. Abstr. 1966, 65, 13794f

MissingFormLabel

12

Shao, M.; Chu, G.; Li, C. unpublished results.