Method for preparing 1-ferrocenyl-3-aryl-3-(ethyl dicarboxylate methine)-acetone

An ethyl dicarboxylate-based methine and ferrocene-based technology, applied in the field of chemical synthesis, can solve the problems of low product yield, accelerated reaction process, inconvenient product purification, etc., and achieves the effect of reducing costs and overcoming non-recovery.

Inactive Publication Date: 2020-02-18
SHAANXI UNIV OF SCI & TECH
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  • Abstract
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Problems solved by technology

The grinding method uses external friction to generate heat to increase the total free energy of the reaction system to activate the system and accelerate the reaction process. However, the grinding method uses alkali as a catalyst to obtain the product after suction filtration. The catalyst cannot be recycled and used, and the cost is high.
Generally, the common solvent method uses a strong base as a catalyst. Due to the violent action of the strong base, many side reactions are often caused, such as self-condensation of the substrate, rearrangement, double addition, further condensation or cracking of the addition product, and reverse Michael addition. , polymerization, etc., resulting in a lower yield of the product, and also brings a lot of inconvenience to the purification of the product

Method used

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  • Method for preparing 1-ferrocenyl-3-aryl-3-(ethyl dicarboxylate methine)-acetone
  • Method for preparing 1-ferrocenyl-3-aryl-3-(ethyl dicarboxylate methine)-acetone
  • Method for preparing 1-ferrocenyl-3-aryl-3-(ethyl dicarboxylate methine)-acetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11- 2

[0044] Preparation of Example 11-ferrocenyl-3-phenyl-3-(ethyl dicarboxylate methine)-acetone:

[0045]

[0046] 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;

[0047] In the second step, after the reaction system is cooled to room temperature, add 0.01mol1-ferrocenyl-3-aryl-propenone and 0.012mol diethyl malonate, slowly heat up, reflux reaction, TLC monitoring until the end of the reaction ( 25min);

[0048] 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-phenyl-3-(ethyl dicarboxylate methine)-acetone . The yield was 83.4%, m.p.: 110-112°C; the filtrate was recovered to obtain a deep eutectic solvent. The yield of the deep eutectic solvent was 83.1% for the first time, 82.8% for the second time, 82.3...

Embodiment 21- 2

[0053] Example 21- Preparation of ferrocenyl-3-(p-bromophenyl)-3-(ethyl dicarboxylate methine)-acetone:

[0054]

[0055] 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;

[0056] In the second step, after cooling the reaction system to room temperature, add 0.01mol 1-ferrocenyl-3-(p-bromophenyl)-propenone and 0.012mol diethyl malonate, slowly heat up, reflux reaction, TLC monitoring To the end of reaction (30min);

[0057] 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-bromophenyl)-3-(ethyl dicarboxylate methine base) - acetone. The yield was 86.6%, m.p.: 116-117°C; the filtrate was recovered to obtain a deep eutectic solvent. The yield of the deep eutectic solvent was 86.4% for the first time, 86% fo...

Embodiment 31- 2

[0062] Example 31- Preparation of ferrocenyl-3-(p-methoxyphenyl)-3-(dicarboxyethyl methine)-acetone:

[0063]

[0064] 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;

[0065] In the second step, after cooling the reaction system to room temperature, add 0.01mol 1-ferrocenyl-3-(p-methoxyphenyl)-propenone and 0.012mol diethyl malonate, slowly heat up, and reflux reaction, TLC monitors to the end of reaction (30min);

[0066] In the third step, the reaction solution is cooled to room temperature, and solids are precipitated, filtered with suction, and the filter cake is washed with a small amount of water to obtain 1-ferrocenyl-3-(p-methoxyphenyl)-3-(ethyl dicarboxylate) methine)-acetone. The yield is 85.8%, m.p.: 135-136°C; the filtrate is recovered to obtain a deep eutectic solvent. The yield of the deep eutectic solvent was 85.4% for the first time, 85.2% for th...

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Abstract

The invention discloses a method for preparing 1-ferrocenyl-3-aryl-3-(ethyl dicarboxylate methine)-acetone, and the method comprises the following steps: adding choline chloride and urea into a dry three-necked flask, and stirring to a transparent solution at 80 DEG C to obtain a deep eutectic solvent; cooling to room temperature, adding ferrocenyl chalcone and diethyl malonate, slowly heating, refluxing for reacting, and performing TLC monitoring until the reaction is finished; cooling the reaction mixture to room temperature, adding a small amount of water, immediately precipitating solids,performing suction filtering, washing the filter cake with water, and drying to obtain the 1-ferrocenyl-3-aryl-(ethyl dicarboxylate methine)-acetone with a yield of over 81%. The filtrate is concentrated and recovered to obtain the deep eutectic solvent, which can be reused. The invention provides a simple, convenient, green and environment-friendly method for the synthesis of the compound, meanwhile, the catalyst can be recycled, and 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-(dicarboxyethylmethine)-acetone. Background technique [0002] Since ferrocenylchalcone has an α,β-unsaturated double bond, most of the reactions about ferrocenylchalcone revolve around the Michael addition reaction. It can undergo Michael addition reaction with hydrazines, thiourea, nitriles, active methylene compounds or amines to generate heterocyclic compounds with ferrocenyl groups, which is useful for the development of more biologically active ferrocenyl groups. Heterocyclic derivatives provide a method. [0003] Most of the existing methods for preparing ferrocenylchalcone are solvent method and solid phase grinding method. The grinding method is to increase the total free energy of the reaction system through external force friction and heat to activate the system and accelerate the reaction process. However, the ...

Claims

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Application Information

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