Improved catalyzed synthesis method for 1,4-dicarbonyl compound

A dicarbonyl compound and synthesis method technology, applied in the field of chemical intermediate synthesis, can solve the problems of low reaction yield, small substrate application range, cumbersome post-treatment, etc.

Active Publication Date: 2014-06-25
SHANDONG FENGYUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] As mentioned above, although there are many preparation methods of 1,4-dicarbonyl compounds in the prior art, these methods still have certain defects, such as the narrow scope of substrate application, low reaction yield, cumbersome post-treatment and many other disadvantages

Method used

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  • Improved catalyzed synthesis method for 1,4-dicarbonyl compound
  • Improved catalyzed synthesis method for 1,4-dicarbonyl compound
  • Improved catalyzed synthesis method for 1,4-dicarbonyl compound

Examples

Experimental program
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Effect test

Embodiment 1

[0038]

[0039] Weigh Cu(acac) according to the molar ratio 1:0.2:0.6 2 , phthalocyanine and 4,4'-dimethyl-2,2'-bipyridine, after they were ground and mixed uniformly, the composite catalyst used in this embodiment was obtained.

[0040] Add 10mmol of compound of formula (I) and 30mmol of compound of formula (II) into the reactor, then sequentially add 50ml of triethylamine, 0.4mmol of composite catalyst, 50mmol of TBHP, seal and incubate at 55°C for 12 hours. After the reaction was completed, the reaction was quenched by adding saturated aqueous sodium thiosulfate solution, the resulting mixture was extracted with ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, and then the extraction solvent was removed by evaporation, and the residue was purified by column to obtain the compound of formula (III), The eluent used for the column purification is a mixture of petroleum ether / ethyl acetate, wherein the volume ratio of petroleum ether to ethyl acet...

Embodiment 2

[0043]

[0044] Weigh Cu(acac) according to the molar ratio 1:0.1:0.8 2 , phthalocyanine and 4,4'-dimethyl-2,2'-bipyridine, after they were ground and mixed uniformly, the composite catalyst used in this embodiment was obtained.

[0045] Add 10mmol of the compound of formula (I) and 20mmol of the compound of formula (II) into the reactor, then sequentially add 40ml of triethylamine, 0.3mmol of composite catalyst, and 40mmol of TBHP, and seal and incubate at 60°C for 10 hours. After the reaction was completed, the reaction was quenched by adding saturated aqueous sodium thiosulfate solution, the resulting mixture was extracted with ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, and then the extraction solvent was removed by evaporation, and the residue was purified by column to obtain the compound of formula (III), The eluent used for the column purification is a mixture of petroleum ether / ethyl acetate, wherein the volume ratio of petroleum eth...

Embodiment 3

[0048]

[0049] Weigh Cu(acac) according to the molar ratio 1:0.3:0.5 2 , phthalocyanine and 4,4'-dimethyl-2,2'-bipyridine, after they were ground and mixed uniformly, the composite catalyst used in this embodiment was obtained.

[0050] Add 10mmol of compound of formula (I) and 10mmol of compound of formula (II) into the reactor, then sequentially add 45ml of triethylamine, 0.1mmol of composite catalyst, 45mmol of TBHP, seal and incubate at 50°C for 15 hours. After the reaction was completed, the reaction was quenched by adding saturated aqueous sodium thiosulfate solution, the resulting mixture was extracted with ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, and then the extraction solvent was removed by evaporation, and the residue was purified by column to obtain the compound of formula (III), The eluent used for the column purification is a mixture of petroleum ether / ethyl acetate, wherein the volume ratio of petroleum ether to ethyl acet...

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Abstract

The invention relates to an improved catalyzed synthesis method for a 1,4-dicarbonyl compound. The method comprises the following steps: adding a compound as shown in a formula I and a compound as shown in a formula II into a reactor; adding triethylamine, a composite catalyst and TBHP (Tert-Butyl Hydroperoxide) in sequence; performing sealed thermal reaction; after reacting, adding a saturated sodium thiosulfate aqueous solution for performing a quenching reaction; extracting the obtained mixture by using ethyl acetate; drying an organic phase by using anhydrous magnesium sulfate; evaporating to remove an extracting solvent; purifying residues by use of a column to obtain the 1,4-dicarbonyl compound as shown in a formula (III). The method is mild in reaction conditions and high in product yield and purity, so that an efficient composite catalytic synthesis method is provided for the preparation of the type of compound, the requirement of preparation of intermediates for use in the fields of organics, chemical industry, medicine and the like is met, and the method has wide industrial application prospect and high market value.

Description

technical field [0001] The invention relates to a synthesis method of a carbonyl compound, in particular to an improved catalytic synthesis method of a 1,4-dicarbonyl compound, and belongs to the field of synthesis of chemical intermediates. Background technique [0002] 1,4-Dicarbonyl compounds are versatile building block units for the synthesis of carbocyclic and heterocyclic compounds, for example, they can be used to construct derivative fragments such as cyclopentenone, furan, thiophene, pyridazine, and pyrrole. It can be seen that the development of a direct and efficient method for preparing 1,4-dicarbonyl compound synthesis units will be of great significance to the progress of organic, chemical, pharmaceutical and other fields. [0003] At present, there are many synthetic methods of 1,4-dicarbonyl compounds or similar compounds in the prior art, such as: [0004] ("Cross-Coupling Reaction ofα-Chloroketones and Organotin Enollates Catalyzed by Zinc Halides for Syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/738C07C67/343C07C67/313C07C235/78C07C231/12C07B41/06B01J31/22
CPCC07B41/06C07C67/313C07C67/343C07C231/12C07C69/738C07C235/78
Inventor 李娜
Owner SHANDONG FENGYUAN CHEM CO LTD
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