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

Abstract

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.

1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

“…The stability of a cone -conformation, in turn, opens new opportunities for the preorganization of functional groups, which is of great advantage in developing of ligands and extractants [ 16 , 17 , 18 ]. The 1,3-diketone derivatives have been well-documented as both promising precursors in organic synthesis [ 19 , 20 ] and as promising compounds in drug design [ 21 , 22 ], although the greatest attention has been focused on their complex ability [ 23 ]. The latter is greatly affected by the structure of 1,3-diketones, since their complexation with metal ions results from the alkaline-driven diketone-to-diketonate transformation undergoing through the keto-enol equilibrium shift.…”