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A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione
Staniszewski, Bartosz and Urbaniak, Włodzimierz A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione Chemical Papers, Vol.63, No. 2, 2009, 212-216
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Document type:
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Článok z časopisu / Journal Article |
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Collection:
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Chemical papers
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| Author(s) |
Staniszewski, Bartosz
Urbaniak, Włodzimierz
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| Title |
A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione
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| Journal name |
Chemical Papers
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| Publication date |
2009
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| Year available |
2009
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| Volume number |
63
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| Issue number |
2
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| ISSN |
0366-6352
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| Start page |
212
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| End page |
216
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2009
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| Language |
english
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| Subject |
250000 Chemical Sciences
250300 Organic Chemistry
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| 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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