A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione

Staniszewski, Bartosz and Urbaniak, WĹ‚odzimierz A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione Chemical Papers, Vol.63, No. 2, 2009, 212-216

Document type: ÄŚlánok z ÄŤasopisu / Journal Article
Collection: Chemical papers  

Author(s) Staniszewski, Bartosz
Urbaniak, WĹ‚odzimierz
Title A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione
Journal name Chemical Papers
Publication date 2009
Year available 2009
Volume number 63
Issue number 2
ISSN 0366-6352
Start page 212
End page 216
Place of publication Poland
Publisher Versita
Collection year 2009
Language english
Subject 250000 Chemical Sciences
250300 Organic Chemistry
Abstract/Summary A novel and efficient method of synthesis of 3-substituted derivatives of pentane-2,4-dione is proposed, wherein cheaper and easily accessible chloro derivatives are conversed into more reactive iodo derivatives. The method is based on the Finkelstein reaction for which the literature suggests highly polar organic solvents as ideal reaction media. In the presented work, the use of industrially used ketones, especially methyl isobutyl ketone, is proposed. The use of MIBK as a solvent additionally allows an azeotropic removal of water from the reaction mixture, enabling the application of moisture sensitive alkylating agents i.e. (3-chloropropyl)trimethoxysilane. The obtained products are isolated through distillation, which does however not allow the separation of C-alkylation products from O-alkylation ones. The products not containing water-sensitive substituents were isolated as copper complexes. The pure product of C-alkylation was obtained by decomposition of the copper complex with a hydrochloric acid solution and extraction of the formed ligand to an organic phase i.e. hexane. The obtained ligand can be further purified by distillation.
 
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