Method for synthesizing 1,4-diketone compound by using 2-halogenated cyclopentanone as raw material

Abstract

The invention provides a method for synthesizing 1,4-diketone compound by using 2-halogenated cyclopentanone as a raw material. In the presence of alkali, 2-halogenated cyclopentanone reacts with silyl enol ether in perfluoroalkyl alcohol used as a solvent to obtain a 1,4-diketone compound, wherein perfluoroalkyl alcohol is trifluoroethanol or hexafluoroisopropanol, and the alkali is selected from sodium carbonate, potassium carbonate, sodium trifluoroethanol, triethylamine and pyrrolidine . The synthesis method provided by the invention has advantages as follows: raw materials are easily available; costs are low; reaction conditions are mild; operation is simple and easy to control; there exists less side reaction; post-treatment is simple; product yield is high; and the solvent can be recovered and recycled so as to greatly save production cost. The method has good environmental protection benefit and economic benefit and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 1,4-diketone compounds, in particular to a preparation method of using 2-chlorocyclopentanone as a raw material to synthesize 1,4-diketone. Background technique [0002] 1,4-diketone compound is an important synthetic intermediate, through which various carbocyclic and heterocyclic compounds can be synthesized, for example, 1,4-diketone compound can be combined with ammonia, ammonium carbonate, alkyl primary amine It can also synthesize pyrrole or substituted pyrrole from many nitrogen-containing compounds; it can also react with phosphorus pentasulfide to form a thiophene ring; it can synthesize furan under the action of acid; it can synthesize oxime ketone (an intermediate for the synthesis of amino acids). At the same time, many natural products and drug molecules contain 1,4-diketone structures, and some 1,4-diketone compounds can be used as solvents in the organic industry. [0003] Although there ...

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Problems solved by technology

[0003] Although there are many methods for synthesizing 1,4-diketone compounds, these methods have certain limitations, such as difficult to obtain raw materials, limited range of substrates, harsh reaction conditions, low yield, complex products and difficult to separate, post-processing, etc. Complex processing, high production cost, etc.

For example: the most commonly used coupling reaction (DeMartino, M.P.; Chen, K.; Baran, P.S. Intermolecular Enolate Heterocoupling: Scope, Mechanism, and Application.J.Am.Chem.Soc. 2008, 130(34), 11546-11560), that is, direct oxidative coupling of ketones through enolization, although this method is currently the most simple and convenient way to synthesize 1,4-diketone compounds, but when different ketones When the compound undergoes oxidative coupling reaction, self-coupling and cross-coupling of the substrate are easy to occur at the same time, resulting in low yield, complex products and difficult separation. Symmetrical 1,4-diketone compounds

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