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Preparation method of 3,7-diethylnonane-4,6-dione

A technology of ethyl nonane and diketone, which is applied in the field of compound preparation, can solve the problems of long-term high-temperature reaction and low-temperature reaction, cumbersome operation steps, and short synthesis process, and achieve mild reaction conditions, convenient operation steps, and easy-to-obtain raw materials Effect

Pending Publication Date: 2019-04-02
SUZHOU SY PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] A preparation method of patent 3,7-diethylnonane-4,6-dione (application number 201810412378.0) uses dimethyl phthalate as raw material, through elimination, addition, catalytic hydrogenation reaction, Brich reduction The preparation of 3,7-diethylnonane-4,6-dione by four-step reaction with ozone oxidation has a short synthesis process, but the operation steps of this method are cumbersome and the safety is low, and metal lithium is required and dangerous. Larger hydrogen, ozone, and long-term high-temperature and low-temperature reactions during the synthesis process

Method used

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  • Preparation method of 3,7-diethylnonane-4,6-dione

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Embodiment 1

[0029] a: Dissolve 1.64g of raw material benzotriazole (14mmol) in 20mL of dichloromethane at 0°C, and add 2.3mL of triethylamine (16mmol) into the reaction system, then drop into 1.93mL of raw material 2 -Ethylbutyryl chloride (14mmol), stirred at 0°C for 4h, after quenching the reaction with 10% HCl solution, continued to stir for 15min, extracted with dichloromethane, and separated by column chromatography to obtain 2.6g of the product 1- Benzotriazole-2-ethyl-1-butanone, the yield is 86%;

[0030] b: Add 5.81g of raw material 2-ethylbutyric acid (50mmol) and 9.75g of N,N'-carbonyldiimidazole (60mmol) into a 100mL reaction flask, dissolve in 20mL of tetrahydrofuran, stir at room temperature for 0.5h, 2-ethyl The reactant of butyric acid and N,N'-carbonyldiimidazole can be reacted more easily, and 5.85g of dimethylhydroxylamine hydrochloride (60mmol) and 7.08g of triethylamine (70mmol) were added in another 50mL reaction bottle , dissolved in 20mL tetrahydrofuran, stirred a...

Embodiment 2

[0034] In a 25mL reaction flask, the 1.15g product 1-benzotriazole-2-ethyl-1-butanone (5.3mmol) and catalyst obtained in step a of Example 1 were dissolved in dichloromethane, Then 0.41 g of the product 3-ethyl-2-pentanone (3.6 mmol) obtained in step c of Example 1 was added dropwise to the reaction system, stirred at room temperature for 3 h, and after quenching the reaction with 10% HCl solution, Extracted with dichloromethane, and separated by column chromatography to obtain 0.47 g of the product 3,7-diethylnonane-4,6-dione, with a yield of 61%.

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Abstract

The invention provides a preparation method of 3,7-diethylnonane-4,6-dione and belongs to the technical field of preparation methods of compounds. The invention includes: performing a reaction on benzotriazole and 2-ethyl butyryl chloride to obtain 1-benzotriazole-2-ethyl-1-butanone; mixing and stirring a 2-ethylbutyric acid / N,N'-carbonyl diimidazole reaction system and a dimethylhydroxylamine hydrochloride / triethylamine reaction system to perform a reaction for preparing 2-ethyl-N-methoxy-N-methylbutyrylamide; at a low temperature condition, performing a reaction on the reactant with methyl magnesium bromide to obtain 3-ethyl-2-pentanone; dissolving the 1-benzotriazole-2-ethyl-1-butanone and a catalyst in a solvent, slowly dropwise adding the 3-ethyl-2-pentanone, stirring the mixture at room temperature, and performing post-treatment to obtain the target product, 3,7-diethylnonane-4,6-dione. The method employs accessible raw materials, is low in preparation cost and high in product yield, and is simple in operations.

Description

technical field [0001] The invention belongs to the technical field of compound preparation methods, and in particular relates to a preparation method of 3,7-diethylnonane-4,6-dione. Background technique [0002] 3,7-diethylnonane-4,6-dione has a unique structure and special properties. It is an important precursor in synthetic chemistry and an important interlayer material in the synthesis of optoelectronic materials. In terms of material chemistry and life science, it has very good development and application prospects. [0003] The synthetic method of 3,7-diethylnonane-4,6-dione has been reported in existing literature, such as Eugene H.Man et al. (Journal of the American Chemical Society, 1951,73,901) A method for synthesizing 3,7-diethylnonane-4,6-dione is reported, which uses 2-ethylbutyric acid as a raw material, and each step is relatively simple, but there are many process steps and the preparation In the process, phenol with high toxicity needs to be used, and ph...

Claims

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Application Information

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IPC IPC(8): C07C45/68C07C49/12
CPCC07C45/004C07C45/68C07C259/06C07D249/18C07C49/12C07C49/04
Inventor 姚梁锋
Owner SUZHOU SY PHARMA TECH CO LTD
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