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
Synthesis 2009(22): 3828-3832
DOI: 10.1055/s-0029-1216992
DOI: 10.1055/s-0029-1216992
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A New and More Efficient Synthesis of Methylene Acetals
Weitere Informationen
Received
18 June 2009
Publikationsdatum:
08. September 2009 (online)
Publikationsverlauf
Publikationsdatum:
08. September 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200922/lookinside/thumbnails/10.1055-s-0029-1216992-1.jpg)
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
-
1a
Williams AA.Lewis MJ.Tucknott OG. Food Chem. 1980, 6: 139 -
1b
Bennett EO. Int. Biodeter. Bull. 1973, 9: 95 -
1c
Dubois JL. inventors; Patent Application EP 1938684. ; Chem. Abstr. 2008, 149, 98879 - 2
Greene TW.Wuts PG. Protective Groups in Organic Synthesis 3rd ed.: Wiley; Indianapolis: 1999. p.201 - 3
Goodwin JC.Hodge JE. Carbohydr. Res. 1973, 28: 213 - 4
Brimacombe JS.Foster AB.Jones BD.Willard JJ. J. Chem. Soc. C 1967, 2404 - 5
Guiso M.Procaccio C.Fizzano MR.Piccioni F. Tetrahedron Lett. 1997, 38: 4291 -
6a
Hanessian S.Yang-Chung G.Lavallee P.Pernet AG. J. Am. Chem. Soc. 1972, 94: 8929 -
6b
Munavu RM. J. Org. Chem. 1980, 45: 3341 - 7
Wang Q.Sun L.Jiang Y.Li C. Beilstein J. Org. Chem. 2008, 4: 51 ; DOI: 10.3762/bjoc.4.51 -
8a
Blotny G. Tetrahedron 2006, 62: 9507 -
8b
Das B.Venateswarlu K.Krishnaiah M. Helv. Chim. Acta 2007, 90: 149 -
8c
Kunishima M.Yamamoto K.Hioki K.Kondo T.Hasegaua M.Tani S. Tetrahedron 2007, 63: 2604 -
8d
Bigdeli MA.Heravi MM.Mahdavinia GH. Catal. Commun. 2007, 8: 1595 - 9
Sun L.Pei G.Niu H.Wang Q.Li C. Synthesis 2008, 3919 -
10a
Suzuki K.Inanaga J.Yamaguchi M. Chem. Lett. 1979, 1277 -
10b
Herz JE.Lucero J.Santoyo Y.Waight ES. Can. J. Chem. 1971, 49: 2418 -
10c
Kaya IA.Jaret RS. J. Chem. Eng. Data 1971, 16: 485 -
10d
Kupchan SM.Casy AF.Swintosky JW. J. Pharm. Sci. 1965, 54: 514 - 11
Wendt GR, andLedig KW. inventors; US Patent 3267120. ; Chem. Abstr. 1966, 65, 13794f
References
Shao, M.; Chu, G.; Li, C. unpublished results.