O-allylation method of alpha,beta-diaryl substituted ethanol

A technology of allylation and diaryl, which is applied in the field of organic synthesis technology, can solve the problems of increased process cost, high reaction temperature, and difficult control, and achieve the effects of less raw material residue, low reaction cost and high economy

Inactive Publication Date: 2020-02-28
武汉回盛生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the laboratory, the specific operation is usually to use strong bases such as sodium hydride, lithium amide, and potassium tert-butoxide to extract hydrogen, and then carry out S N 2 Substitution reaction to prepare the corresponding alkyl-alkyl ether must use anhydrous reaction conditions, otherwise the reaction will be very poor, or even no conversion; due to anhydrous conditions, industrial production, especially in large quantities, is more difficult to control and costs more
In industrial production, the use of phase transfer catalysts can effectively avoid the requirement of anhydrous conditions. However, in order to achieve good results, the screening of phase transfer catalysts is very important. Many phase transfer catalysts with good effects are relatively expensive, and the reaction of the system The temperature is generally higher, and the complete removal of the post-treatment phase transfer catalyst also increases the process cost

Method used

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  • O-allylation method of alpha,beta-diaryl substituted ethanol
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  • O-allylation method of alpha,beta-diaryl substituted ethanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] O-allylation of substrate S1:

[0041]

[0042] Dissolve substrate S1 (25.71g, 100mmol) in 100mL dimethyl sulfoxide at room temperature, dissolve 8.42g (150mmol) potassium hydroxide in 22mL water, wait until the temperature drops to room temperature, and then slowly add it dropwise to the above S1 In the dimethyl sulfoxide solution, the temperature of the mixed solution was controlled below 40°C during the dropwise addition, and the reaction was stirred at 35°C for 1 hour after the dropwise addition was completed. Then slowly drop into it a chloropropene solution (8.42g chloropropene is dissolved in 25mL dimethyl sulfoxide), control the rate of addition to maintain the temperature of the reaction solution at 35-40°C, and after the dropwise addition is completed, the reaction temperature will be 35-40°C. Continue to stir the reaction under low temperature. When the liquid phase detection shows that the remaining raw materials are less than 2%, the system is cooled to ...

Embodiment 2

[0045] O-allylation of substrate S2:

[0046]

[0047] Substrate S2 (3.76g, 20mmol) was dissolved in 20mL dimethyl sulfoxide at room temperature, 1.60g (40mmol) sodium hydroxide was dissolved in 5mL water and cooled to room temperature, then slowly added dropwise to the above S2 dimethyl In the base sulfoxide solution, the temperature of the mixed solution was controlled below 40°C during the dropwise addition, and the reaction was stirred at 35°C for 1 hour after the dropwise addition was completed. Then slowly drop into it a chloropropene solution (1.70g chloropropene dissolved in 5mL dimethyl sulfoxide), control the rate of addition to maintain the temperature of the reaction solution at 35-40°C, Continue to stir the reaction, after the TLC detection of complete conversion of the raw materials, cool the system to 0°C, add water to quench the reaction, then extract with ethyl acetate, combine the organic phases, wash with salt water, wash with water, dry over anhydrous so...

Embodiment 3

[0049]O-allylation of substrate S5:

[0050]

[0051] Substrate S5 (2.23g, 10mmol) was dissolved in 20mL dimethyl sulfoxide at room temperature, 0.84g (15mmol) potassium hydroxide was dissolved in 5mL water and cooled to room temperature, then slowly added dropwise to the above S5 dimethyl In the base sulfoxide solution, the temperature of the mixed solution was controlled below 40°C, and the reaction was stirred at 35°C for 1 hour after the dropwise addition was completed. Then slowly drop allyl chloride solution (1.00g allyl chloride dissolved in 5mL dimethyl sulfoxide) to it, control the rate of addition to maintain the temperature of the reaction solution at 35-40°C, Continue to stir the reaction, after the TLC detection of complete conversion of the raw materials, cool the system to 0°C, add water to quench the reaction, then extract with ethyl acetate, combine the organic phases, wash with salt water, wash with water, dry over anhydrous sodium sulfate, concentrate, an...

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Abstract

The invention belongs to the technical field of organic synthesis technology, and specifically discloses an O-allylation method of alpha,beta-diaryl substituted ethanol. The method has the advantagesof mild reaction conditions, simple and convenient operation, and low equipment requirement, is suitable for industrial amplification, and belongs to the field of organic synthesis. According to the method, an inorganic alkali / dimethyl sulfoxide hyper-alkaline system is used to activate an alcohol substrate, and then the substrate reacts with allyl chloride. Compared with the prior art, the methodhas the advantages of quick reaction speed, high yield, mild conditions, low equipment requirements, simple and convenient operation, green, and safety, is especially suitable for industrial enlargedproduction, and has an important industrial application value; and the cost advantage is prominent.

Description

technical field [0001] The invention relates to the technical field of organic synthesis technology, in particular to a method for O-allylation of α,β-diaryl substituted ethanol. The method has the advantages of mild conditions, simple operation, low equipment requirements, and is suitable for industrial scale-up. Background technique [0002] Ether structures widely exist in drug molecules, and the Williamson ether formation method is often used to construct ether bonds. In the laboratory, the specific operation is usually to use strong bases such as sodium hydride, lithium amide, and potassium tert-butoxide to extract hydrogen, and then conduct S N 2 Substitution reaction to prepare the corresponding alkyl-alkyl ether must use anhydrous reaction conditions, otherwise the reaction will be poor, or even no conversion; due to anhydrous conditions, industrial production, especially in large quantities, is more difficult to control and costs more. In industrial production, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60C07D213/30C07C41/16C07C43/164C07C43/174C07C41/18C07C43/205
CPCC07C41/16C07C41/18C07D213/30C07D233/60C07C43/164C07C43/174C07C43/1742C07C43/2055
Inventor 张卫元彭康洲孙凯成梦雅陈骁李钰
Owner 武汉回盛生物科技股份有限公司
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