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Method for preparing 1-ferrocenyl-3-aryl-3-diacetyl methylene-acetone

A technology of diacetylmethine and ferrocene, applied in the field of chemical synthesis, can solve the problems of large amount of strong base, low yield, and inability to recycle and use, and achieves overcoming the large amount of consumption, low cost of raw materials, and ease of use. the effect obtained

Active Publication Date: 2020-01-24
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The grinding method is to increase the total free energy of the reaction system through external friction and heat to activate the system and accelerate the reaction process. However, the amount of strong alkali used as a catalyst in the grinding method is large and cannot be recycled, and the cost is high.
Generally, the common solvent method uses a strong base as a catalyst, which has the disadvantages of long preparation reaction time, low yield, and large amount of solvent used.

Method used

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  • Method for preparing 1-ferrocenyl-3-aryl-3-diacetyl methylene-acetone
  • Method for preparing 1-ferrocenyl-3-aryl-3-diacetyl methylene-acetone
  • Method for preparing 1-ferrocenyl-3-aryl-3-diacetyl methylene-acetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11- 2

[0043] Preparation of Example 11-ferrocenyl-3-phenyl-3-diacetylmethine-acetone:

[0044]

[0045] In the first step, add 1mol choline chloride and 2mol urea to the reaction vessel, stir at 80°C until completely dissolved to obtain a deep eutectic solvent;

[0046] In the second step, after cooling the reaction system to room temperature, add 0.01mol 1-ferrocenyl-3-aryl-propenone and 0.012mol 2,4-pentanedione, slowly heat up, reflux reaction, TLC monitoring until the end of the reaction (25min);

[0047] In the third step, the reaction solution was cooled to room temperature, and a solid was precipitated, which was suction filtered, and the filter cake was washed with a small amount of water to obtain 1-ferrocenyl-3-phenyl-3-diacetylmethine-acetone. The yield was 83.4%, m.p.: 106-108°C; the filtrate was recovered to obtain a deep eutectic solvent. The yield of the deep eutectic solvent was 83.2% for the first time, 83% for the second time, 82.8% for the third time, and 82....

Embodiment 21- 2

[0052] Example 21- Preparation of ferrocenyl-3-(p-fluorophenyl)-3-diacetylmethine-acetone:

[0053]

[0054] In the first step, add 1mol choline chloride and 2mol urea to the reaction vessel, stir at 80°C until completely dissolved to obtain a deep eutectic solvent;

[0055] In the second step, after cooling the reaction system to room temperature, add 0.01mol 1-ferrocenyl-3-(p-fluorophenyl)-propenone and 0.012mol 2,4-pentanedione, slowly heat up, reflux reaction, TLC Monitor until the end of the reaction (25min);

[0056] In the third step, the reaction liquid is cooled to room temperature, and a solid is precipitated, filtered with suction, and the filter cake is washed with a small amount of water to obtain 1-ferrocenyl-3-(p-fluorophenyl)-3-diacetylmethine-acetone . The yield is 91%, m.p.: 151-153°C; the filtrate is recovered to obtain a deep eutectic solvent. The yield of the deep eutectic solvent was 89.9% for the first time, 89.5% for the second time, 89.1% for the t...

Embodiment 31- 2

[0061] Example 31- Preparation of ferrocenyl-3-(p-chlorophenyl)-3-diacetylmethine-acetone:

[0062]

[0063] In the first step, add 1mol choline chloride and 2mol urea to the reaction vessel, stir at 80°C until completely dissolved to obtain a deep eutectic solvent;

[0064] In the second step, after cooling the reaction system to room temperature, add 0.01mol 1-ferrocenyl-3-(p-chlorophenyl)-propenone and 0.012mol 2,4-pentanedione, slowly heat up, reflux reaction, TLC Monitor until the end of the reaction (30min);

[0065] In the third step, the reaction solution was cooled to room temperature, and a solid was precipitated, filtered with suction, and the filter cake was washed with a small amount of water to obtain 1-ferrocenyl-3-(p-chlorophenyl)-3-diacetylmethine-acetone . The yield was 93.2%, m.p.: 147-149°C; the filtrate was recovered to obtain a deep eutectic solvent. The yield of the deep eutectic solvent was 93% for the first time, 92.8% for the second time, 92.5% ...

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Abstract

The invention discloses a method for preparing 1-ferrocenyl-3-aryl-3-diacetyl methine-acetone. The method comprises the following steps: adding choline chloride and urea into a dry three-neck flask, and stirring at 80 DEG C to obtain a transparent solution, thereby obtaining an deep eutectic solvent; cooling the deep eutectic solvent to room temperature, adding ferrocenyl chalcone and 2, 4-pentanedione, slowly heating, carrying out reflux reaction, and carrying out TLC monitoring until the reaction is finished; cooling an obtained reaction mixed liquid to room temperature, adding a small amount of water, immediately separating out solids, carrying out suction filtration, washing an obtained filter cake with water, and drying to obtain 1-ferrocenyl-3-aryl-3-diacetyl methylene-acetone; wherein the deep eutectic solvent (DES) can be obtained by concentrating and recovering an obtained filtrate, can be repeatedly used for five times, and the catalytic activity of the DES is not obviously reduced. The method is simple to operate, short in reaction time, high in yield and simple in aftertreatment, and meanwhile, the catalyst can be recycled, so that the reaction cost is reduced.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a method for preparing 1-ferrocenyl-3-aryl-3-diacetylmethine-acetone. Background technique [0002] Chalcones belong to brass compounds, which are a common class of compounds in natural products, and have corresponding pharmaceutical activities. Synthetic chalcones are mostly synthesized by inorganic bases, inorganic acid metal organic compounds, microwave, ultrasonic catalysis and other methods. Ferrocenyl-containing chalcones are generally synthesized by Claisen-Schmidt condensation reaction. Its molecular structure has good conjugation and good electron mobility. It can be used as a nonlinear organic optical material and has good biological activity. It is an important class of organic pharmaceutical intermediates, which can be used for antibacterial, anti-inflammatory, anti-ulcer, anti-allergic, etc. [0003] Ferrocenyl chalcone contains α, β unsaturated double b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02B01J31/02
CPCC07F17/02B01J31/0239B01J31/0271B01J31/0249B01J2231/32Y02P20/584
Inventor 刘玉婷孙嘉希尹大伟李洁
Owner SHAANXI UNIV OF SCI & TECH
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