Catalytic synthesis method of organic chemical intermediate 1,2-diketone compound

A synthesis method and compound technology are applied in the fields of catalytic synthesis of organic chemical intermediates 1,2-diketone compounds and catalytic oxidation of aryl alkyl alkynes to prepare 1,2-diketone compounds, which can solve the problem of narrow bottom The scope of application of chemical substances, inability to fully meet the problems, low reaction yield and chemical selectivity, etc., to overcome the poor catalytic performance.

Active Publication Date: 2014-07-23
河北德瑞化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although the prior art has reported a variety of synthesis methods for the preparation of 1,2-diketones by oxidation of alkyne compounds, these methods have many inherent defects, such as harsh reaction conditions, narrow substrate scope, low The reaction yield and chemoselectivity of these processes or methods cannot fully meet the needs of contemporary industrial production.

Method used

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  • Catalytic synthesis method of organic chemical intermediate 1,2-diketone compound
  • Catalytic synthesis method of organic chemical intermediate 1,2-diketone compound
  • Catalytic synthesis method of organic chemical intermediate 1,2-diketone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add 1mmol formula (I) compound and 12ml acetone in the reactor at room temperature, then slowly add 2.2mmol mercuric acetate and 2.2mmol water, then add 70mg of ferrocene with a mass ratio of 0.2:0.25:1 while stirring , salicylic acid and triethyloxonium tetrafluoroborate additive mixture, after mixing, continue to stir the reaction for 0.5h, monitor the reaction end point by TLC, add an equal volume of water to the system after the reaction is completed, and then use ethyl acetate The ester was extracted three times, the organic phase was combined, and the organic phase was washed with 1 / 2 volume of saturated brine, the organic phase was separated, dried by adding anhydrous sodium sulfate, filtered, and finally the organic solvent was removed by vacuum distillation, and the residue was purified by silica gel column chromatography , the compound of formula (II) can be obtained with a yield of 98.6% and a purity of 99.1% (HPLC).

[0033] 1 H NMR (500MHz, CDC...

Embodiment 2

[0035]

[0036] Add 1mmol formula (I) compound and 15ml acetone in reactor at room temperature, then slowly add 2.5mmol mercuric acetate and 2.5mmol water, then add 62mg of ferrocene in a mass ratio of 0.2:0.25:1 while stirring , salicylic acid and triethyloxonium tetrafluoroborate additive mixture, after mixing, continue to stir the reaction for 1.5h, monitor the reaction end point by TLC, add an equal volume of water to the system after the reaction is completed, and then use ethyl acetate The ester was extracted three times, the organic phase was combined, and the organic phase was washed with 1 / 2 volume of saturated brine, the organic phase was separated, dried by adding anhydrous sodium sulfate, filtered, and finally the organic solvent was removed by vacuum distillation, and the residue was purified by silica gel column chromatography , the compound of formula (II) can be obtained with a yield of 98.8% and a purity of 99.3% (HPLC).

[0037] 1 H NMR (400MHz, CDCl 3 ) δ...

Embodiment 3

[0039]

[0040] Add 1mmol formula (I) compound and 13ml acetone in reactor at room temperature, then slowly add 2.3mmol mercuric acetate and 2.3mmol water, then add 65mg of ferrocene with a mass ratio of 0.2:0.25:1 while stirring , salicylic acid and triethyloxonium tetrafluoroborate additive mixture, after mixing, continue to stir the reaction for 2h, monitor the reaction end point by TLC, add an equal volume of water to the system after the reaction is completed, and then use ethyl acetate Extract three times, combine the organic phase, add 1 / 2 volume of saturated brine to wash the organic phase, separate the organic phase, add anhydrous sodium sulfate to dry, filter, and finally remove the organic solvent by vacuum distillation, and the residue is purified by silica gel column chromatography. The compound of formula (II) can be obtained with a yield of 98.9% and a purity of 99.2% (HPLC).

[0041] 1 H NMR (500MHz, CDCl 3 )δ=7.94(d, J=8.8Hz, 2H), 6.92(d, J=8.8Hz, 2H), 6....

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Abstract

The invention relates to a catalytic synthesis method of an organic chemical intermediate 1,2-diketone compound. Asymmetric aryl alkyl acetylene is taken as a raw material, direct catalytic oxidation reaction is achieved in the presence of a multi-component catalyst/assistant system, so as to prepare the 1,2-diketone compound. Effects of types of components of the catalyst and the assistant are researched by a lot of experiments, and a reaction solvent applicable to the system is properly screened. The synthesis process is high in reaction yield, mild in reaction condition and short in reaction time, is an excellent synthesis method of the 1,2-diketone compound, and has broad large-scale industrial application value and market potential.

Description

technical field [0001] The present invention relates to a catalytic synthesis method of an organic chemical intermediate 1,2-diketone compound, more specifically to a method for preparing a 1,2-diketone compound by catalytic oxidation of an aryl alkyl alkyne, which belongs to the organic Chemical synthesis field. Background technique [0002] The 1,2-diketone structure is an important structural fragment of many bioactive molecules. It is widely used in the preparation of complex compounds in organic synthesis, and has attracted extensive attention from researchers in the fields of medicine, biology, and organic synthesis. [0003] Traditional methods for the preparation of 1,2-diketones mainly involve the oxidation or catalytic oxidation of diaryl alkynes. As early as the 1970s, N.S.Srinivasan et al. ("Preparation of1,2-Diketones: Oxidation of Alkynes by Potassium Permanganate in Aqueous Acetone", J.Org.Chem., 44(9), 1574) reported an acetone aqueous solution A method for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07C221/00C07C225/22C07C45/28C07C49/76C07C49/825C07C49/807
Inventor 魏建华
Owner 河北德瑞化工有限公司
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