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Preparation method of 3-(4-chlorphenyl)-1, 5-diphenylpentane-1, 5-diketone compound

A technology of diphenylpentane and chlorophenyl, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of harsh reaction conditions, unfriendly environment, and limited application, and achieve the effect of simple preparation method, low price, and wide application

Pending Publication Date: 2022-05-06
JINGCHU UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The compound 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione is an important compound for the synthesis of pyrazolo[1,5-α]pyrimidines such as zaleplon. Intermediates, at present, for the synthesis of the intermediates, more expensive raw materials are mostly used, or the reaction conditions are relatively harsh, or the yield is low, and at the same time, they are not friendly to the environment, which greatly limits their industrial application

Method used

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  • Preparation method of 3-(4-chlorphenyl)-1, 5-diphenylpentane-1, 5-diketone compound
  • Preparation method of 3-(4-chlorphenyl)-1, 5-diphenylpentane-1, 5-diketone compound

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Experimental program
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Embodiment 1

[0021] Embodiment 1: the preparation of iron complex catalyst

[0022] At room temperature, 4′-chlorophenyl-2,2′:6′,2′′-terpyridine (10 mmol) was dissolved in tetrahydrofuran (20 mL), and anhydrous ferrous chloride ( 10 mmol). After the mixed solution was stirred overnight, it was filtered, and the obtained solid was washed three times with tetrahydrofuran, and then dried to obtain an iron metal complex catalyst. Yield: 87.3%.

Embodiment 2

[0023] Example 2: Synthesis of 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione

[0024] Iron metal complex catalyst (2mmol, 0.941g) and potassium tert-butoxide (10mmol, 1.12g) were dissolved in 30mL xylene at room temperature, then 4-chlorobenzyl alcohol (110mmol, 15.62g) and acetophenone ( 100mmol, 12g), then reflux reaction for 24h, after the reaction, cooled to room temperature, and removed the solvent. The resulting mixture was separated by column chromatography to obtain a pure product, that is, 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione was obtained. Yield is 91.2%, characterization data: 1 H NMR (400 MHz, CDCl 3 ) ,ppm,δ :7.95 (d, J =7.6 Hz, 4 H), 7.56-7.53 (M, 2 H), 7.45-7.43 (m, 4H), 7.28-7.24 (m, 4 H), 4.08 ( J = 7.0 Hz, 1 H), 3.48 (dd, J = 6.9 Hz, 2 H),3.32 (dd, J =7.3 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ) ,ppm,δ: 198.2, 142.3,136.8, 133.2,132.4, 129.0,128.9, 128.72, 128.6, 44.7, 36.5.

Embodiment 3

[0025] Example 3: Synthesis of 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione

[0026] Iron metal complex catalyst (2mmol, 0.941g) and potassium tert-butoxide (10mmol, 1.12g) were dissolved in 30mL xylene at room temperature, then 4-chlorobenzyl alcohol (60mmol, 8.52g) and acetophenone ( 100mmol, 12g), then reflux reaction for 24h, after the reaction, cooled to room temperature, and removed the solvent. The resulting mixture was directly washed with petroleum ether to obtain 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione. Yield is 89.5%, characterization data: 1 H NMR (400 MHz, CDCl 3 ) ,ppm,δ :7.95 (d, J =7.6 Hz, 4 H), 7.56-7.53 (M, 2 H), 7.45-7.43 (m, 4 H), 7.28-7.24 (m, 4 H), 4.08 ( J = 7.0 Hz, 1 H), 3.48 (dd, J = 6.9 Hz, 2 H), 3.32 (dd, J =7.3 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ), ppm, δ: 198.2, 142.3, 136.8, 133.2, 132.4, 129.0, 128.9, 128.72, 128.6, 44.7, 36.5.

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Abstract

The chemical structural formula of the 3-(4-chlorphenyl)-1, 5-diphenylpentane-1, 5-diketone compound is shown in the specification, and a preparation method of the 3-(4-chlorphenyl)-1, 5-diphenylpentane-1, 5-diketone compound comprises the following steps: A, dissolving 4 '-chlorphenyl-2, 2': 6 ', 2' '-terpyridyl in tetrahydrofuran under the condition of room temperature, adding anhydrous ferrous chloride under the protection of nitrogen, stirring, filtering, and drying to obtain 4'-chlorphenyl-2, 2 ': 6', 2 ''-terpyridyl; and washing the obtained solid with tetrahydrofuran, drying, and collecting the solid to obtain the iron metal complex catalyst. And B, dissolving an iron metal complex catalyst and potassium tert-butoxide in a solvent at room temperature, then adding 4-chlorobenzyl alcohol and acetophenone, then carrying out a reflux reaction, removing the solvent, and purifying to obtain the 3-(4-chlorphenyl)-1, 5-diphenylpentane-1, 5-diketone. The preparation method is simple and convenient, low in price, high in yield, suitable for large-scale synthesis and suitable for industrial production and application. The method is wide in application and can be used for preparing various drug intermediates.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical intermediates, and relates to a preparation method of 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione compound. Background technique [0002] Pyrazolo[1,5-α]pyrimidines are a class of heterocyclic compounds with high activity, which have anti-tumor, bactericidal, sedative and anti-cardiovascular effects, and also have herbicidal and insecticidal effects in the field of pesticides . Therefore, pyrazolo[1,5-a]pyrimidines have become a research hotspot in medicine and pesticide chemistry. [0003] The compound 3-(4-chlorophenyl)-1,5-diphenylpentane-1,5-dione is an important compound for the synthesis of pyrazolo[1,5-α]pyrimidines such as zaleplon. Intermediates, for the synthesis of these intermediates, most of them have adopted more expensive raw materials, or the reaction conditions are relatively harsh, or the yield is low, and at the same time, they are not friendly to the environmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/813C07C45/68B01J31/22
CPCC07C45/68B01J31/1815B01J2531/842B01J2531/0238B01J2231/4205C07C49/813Y02P20/584
Inventor 刘娥李立威王洪林张华新
Owner JINGCHU UNIV OF TECH