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Method for reducing diyne compounds

A compound, the technology of borane dimethyl sulfide, which is applied in the field of reducing diacetylenic compounds, can solve the problems of high price, large amount of tetrahydrofuran borane solution, low concentration of borane tetrahydrofuran solution, etc., and achieve the effect of improving efficiency

Active Publication Date: 2014-11-05
WATERSTONE PHARMA WUHAN
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

At present, most of the methods for preparing diene compounds by reducing diacetylenic compounds use borane tetrahydrofuran solution or borane nitrogen nitrogen dimethylaniline complex to reduce diacetylene compounds, but borane nitrogen nitrogen diethylaniline The borane complex is expensive, and the amount of borane is too large, which is not convenient for industrial production. In addition, the concentration of borane tetrahydrofuran solution is low. Currently, there is only 1M borane tetrahydrofuran solution on the market, resulting in a large amount of tetrahydrofuran borane solution. The price is also more expensive, and the reaction volume is relatively large, resulting in low volume utilization of the reactor
[0003] Therefore, the current method for reducing diacetylenic compounds still needs to be improved.

Method used

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  • Method for reducing diyne compounds

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preparation example Construction

[0042] (1) Preparation of a system of borane reagent and tetrahydrofuran

[0043] Adding tetrahydrofuran into the reaction bottle, and then replacing the tetrahydrofuran with nitrogen, and then, under the protection of nitrogen, mixing the borane dimethyl sulfide solution and the nitrogen-substituted tetrahydrofuran to obtain a system of borane reagent and tetrahydrofuran.

[0044] (2) Synthesis of borane system containing active hydrogen

[0045] Cool the system of borane reagent and tetrahydrofuran obtained above to 0-10°C, then slowly add cyclohexene dropwise to the system of borane reagent and tetrahydrofuran, white solids will precipitate during the dropping process, and control The maximum temperature does not exceed 12°C. After the dropwise addition, the obtained mixture is kept at 0-10° C. for 3-5 hours to obtain a borane system containing active hydrogen, and this step does not need to be monitored.

[0046] (3) Synthesis of Diene Compounds

[0047] Cool the borane...

Embodiment 1

[0049] a. Synthesis of borane system containing active hydrogen

[0050] Add 150g (2.08mol) of tetrahydrofuran into a 500mL reaction flask, replace with nitrogen three times, add 35mL (0.35mol) of borane dimethyl sulfide solution under nitrogen protection, cool down to 0°C, and slowly add cyclohexene 63.3g (0.77 mol), the temperature was controlled not to exceed 12°C, and after the dropwise addition was completed, the reaction was incubated for 5 hours, and the reaction was stopped to obtain a borane system containing active hydrogen.

[0051] b. Reduction of 15,15-diethoxyhexadecyl-3,5-diyne

[0052] Cool the borane system containing active hydrogen obtained above to -10°C, slowly add 29.2 g (0.1 mol) of 15,15-diethoxyhexadecyl-3,5-diyne dropwise, after the dropwise addition is completed, Stir the reaction at -5-0°C for 5 hours, then raise the temperature to 5-10°C, stir the reaction for 4 hours, follow the reaction process by GC, control the raw material to be less than 1.5...

Embodiment 2

[0054] a. Synthesis of active hydrogen borane system

[0055] Add 150g (2.08mol) of tetrahydrofuran (THF) into a 500mL reaction flask, replace with nitrogen three times, add 40mL (0.4mol) of borane dimethyl sulfide solution under nitrogen protection, cool down to 10°C, and slowly add cyclohexene 69.8g (0.85 mol), control the temperature not to exceed 12°C, react for 4 hours after the dropwise addition, and stop the reaction to obtain a borane system containing active hydrogen.

[0056] b. Reduction of 15,15-diethoxyhexadecyl-3,5-diyne

[0057] Cool the borane system containing active hydrogen obtained above to -10°C, slowly add 29.2 g (0.1 mol) of 15,15-diethoxyhexadecyl-3,5-diyne dropwise, after the dropwise addition is completed, Stir the reaction at -5-0°C for 5 hours, then raise the temperature to 5-10°C, stir the reaction for 4 hours, follow the reaction process by GC, control the raw material to be less than 1.5% (full integral), after the reaction is qualified, add 120...

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Abstract

The invention provides a method for reducing diyne compounds. The method for reducing the compounds represented by a formula I comprises the following steps: (1) a system of a borane reagent and tetrahydrofuran is provided, wherein the borane reagent is a borane dimethylsulfide solvent; (2) cyclohexene is dropped into the system of borane reagent and tetrahydrofuran, such that a borane system comprising active hydrogen is obtained; (3) the compound represented by the formula I is added into the borane system comprising active hydrogen, and a reduction reaction is carried out, such that a compound represented by a formula II can be obtained. With the method, diyne compounds can be effectively reduced into diene compounds. In the entire process of the method, reaction materials are easy to obtain; reaction post-treatment is simple; industrial three-waste treatment is easy; and target product yield is high. The method is suitable for industrialized productions.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular, the invention relates to a method for reducing diacetylenic compounds. Background technique [0002] Diene compounds are widely used in chemicals, such as some pheromones are diene compounds. Related literatures report that there are many methods for synthesizing diene compounds, for example, diene compounds can be prepared by reduction of diacetylenic compounds. At present, most of the methods for preparing diene compounds by reducing diacetylenic compounds use borane tetrahydrofuran solution or borane nitrogen nitrogen dimethylaniline complex to reduce diacetylene compounds, but borane nitrogen nitrogen diethylaniline The borane complex is expensive, and the amount of borane is too large, which is not convenient for industrial production. In addition, the concentration of borane tetrahydrofuran solution is low. Currently, there is only 1M borane tetrahydrofuran solution on the ...

Claims

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Application Information

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IPC IPC(8): C07B35/02C07C41/20C07C43/15C07C5/09C07C11/12
Inventor 王念乔凌翔崔健宋伟张志海
Owner WATERSTONE PHARMA WUHAN
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