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-00000084.xml
Synthesis 2005(11): 1775-1778
DOI: 10.1055/s-2005-865318
DOI: 10.1055/s-2005-865318
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Method for the Protection of Alcohols and Phenols by Using Hexamethyldisilazane in the Presence of Cupric Sulfate Pentahydrate under Neutral Reaction Conditions
Further Information
Received
31 January 2005
Publication Date:
18 April 2005 (online)
Publication History
Publication Date:
18 April 2005 (online)
Abstract
Alcohols and phenols are protected with hexamethyldisilazane in the presence of cupric sulfate pentahydrate in good to excellent yields in acetonitrile. The method is highly selective for the conversion of primary alcohols in the presence of secondary and tertiary alcohols as well as phenols.
Keywords
cupric sulfate pentahydrate - HMDS - alcohol - phenol - trimethylsilylether
- 1
Bruynes CA.Jurriens TK. J. Org. Chem. 1982, 47: 3966 - 2
Langer SH.Connell S.Wender J. J. Org. Chem. 1958, 23: 50 - 3
Guttret P.El-Ghamarti S.Legrand A.Coutrier D.Rigo B. Synth. Commun. 1996, 26: 707 - 4
Goldschmidt AG. inventors; German Patent 275884. ; Chem. Abstr. 1979, 90, 65300 - 5
Firouzabadi H.Karimi B. Synth. Commun. 1993, 23: 1633 - 6
Firouzabadi H.Sardarian AR.Khayat Z.Karimi B.Tangestaninejad H. Synth. Commun. 1997, 27: 2709 - 7
Curini M.Epifano F.Marcotullio MC.Rosati O.Constantino U. Synth. Commun. 1999, 29: 541 - 8
Zhang H.Li TS.Yang F.Fu CG. Synth. Commun. 1998, 28: 3105 - 9
Zuercher K.Hadorn H. Dtsch. Lebensm.-Rundsch. 1975, 71: 68 - 10
Bauer I. inventors; German Patent 2507882. ; Chem. Abstr. 1977, 86, 43810g - 11
Harrp DN.Steliou K.Chan TH. J. Am. Chem. Soc. 1978, 100: 1222 - 12
Lalonde M.Chan TH. Synthesis 1985, 817 -
13a
Karimi B.Golshani B. J. Org. Chem. 2000, 65: 7228 -
13b
Firouzabadi H.Iranpoor N.Sobhani S. Tetrahedron Lett. 2002, 43: 3653 - 14
Firouzabadi H.Iranpoor N.Amani K.Nowrouzi F. J. Chem. Soc., Perkin Trans. 1 2002, 2601 -
15a
Akhlaghinia B.Asadi M.Safaei E.Heydarpoor M. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179: 2099 -
15b
Akhlaghinia B.Asadi M.Safaei E.Heydarpoor M. J. Porphyrins Phthalocyanines 2004, 8: 1285 -
15c
Akhlaghinia B.Pourali AR. Synthesis 2004, 1747 -
15d
Akhlaghinia B. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179: 1783