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Method for preparing (E)-3-ethyl acrylate pinaborate

A technology of ethyl acrylate and naborate, which is applied in the field of organic chemical synthesis, can solve problems such as difficulty in purchasing organophosphorus ligands, high production costs, and expensive products, and achieve cheap raw materials, low product costs, The effect of high yield

Inactive Publication Date: 2015-05-13
成都安斯利生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantages of this method are: the organophosphorus ligand is not easy to buy, the price is expensive, the reaction is strongly exothermic, and the reaction is carried out in a sealed tube, only a few grams of the target product can be synthesized, and it is impossible to realize scale-up production at all. Commercialization, high production cost, high product price

Method used

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  • Method for preparing (E)-3-ethyl acrylate pinaborate
  • Method for preparing (E)-3-ethyl acrylate pinaborate

Examples

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Effect test

Embodiment 1

[0021] In a 1L three-necked reaction flask, add D-α-pinene (50g, 0.37mol) and 200mL of anhydrous tetrahydrofuran. 0.17mol, 10M in dimethyl sulfide), after the addition, the temperature was raised to room temperature, and reacted for 4h to generate a white solid, then the reaction solution was cooled to -40°C, and the tetrahydrofuran solution of ethyl propiolate (17.3g, 0.17mol), the addition was completed, and after rising to room temperature, reacted for 12h, added anhydrous acetaldehyde (75g, 1.7mol), heated to 40°C and reacted for 17h, cooled to room temperature, removed excess anhydrous acetaldehyde under reduced pressure, and then added Pinacol (20g, 0.17mol), stirred at room temperature for 6h, evaporated the solvent under reduced pressure with a rotary evaporator to generate a yellow liquid, and then collected 78-80°C / 1mmHg fractions by distillation under reduced pressure to obtain 32.4g of colorless liquid , which is (E)-3-ethyl acrylate pinaborate with a yield of 78%....

Embodiment 2

[0023] In a 10L three-necked reaction flask, add D-α-pinene (2331.15g, 17.11mol) and 2L anhydrous tetrahydrofuran, under the protection of nitrogen, cool to 0°C, slowly add borane dimethyl sulfide complex (815mL , 8.15mol, 10M in dimethyl sulfide), after the addition, the temperature was raised to room temperature, reacted for 4h, and a white solid was generated, then the reaction solution was cooled to -40°C, and a tetrahydrofuran solution of ethyl propiolate (800g, 8.15mol), the addition was completed, and after rising to room temperature, reacted for 12h, added anhydrous acetaldehyde (3690g, 81.5mol), heated to 40°C and reacted for 17h, cooled to room temperature, removed excess anhydrous acetaldehyde under reduced pressure, and then added Pinacol (963.1g, 8.15mol), stirred at room temperature for 6h, evaporated the solvent under reduced pressure with a rotary evaporator to generate a yellow liquid, and then collected 78-80°C / 1mmHg fractions by distillation under reduced pre...

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Abstract

The invention discloses a method for preparing a medical intermediate (E)-3-ethyl acrylate pinaborate. The method specifically comprises the following steps: preparing di-alpha-pinoborane by using dextro-alpha-pinene and a borane-dimethyl sulfide complex as raw materials, then reacting di-alpha-pinoborane with ethyl propiolate at room temperature, then using anhydrous acetaldehyde for reduction to generate dimethyl borate and then reacting dimethyl borate with pinacol to generate (E)-3-ethyl acrylate pinaborate. The method has the obvious advantages that the reaction raw materials are easy to obtain; the reaction operation is simple; large-scale production is easy to achieve; the yield is high; the purity is good; the production cost is low.

Description

technical field [0001] The invention relates to a new method for synthesizing a medical intermediate organic borate, belonging to the field of organic chemical synthesis, in particular to a new method for preparing (E)-3-ethyl acrylate pinaborate. Background technique [0002] Organic boronic esters are an important class of pharmaceutical intermediates and organic chemical reagents, widely used in organic synthesis to form new C-C single bonds through Suzuki-Miyaura coupling reactions. In particular, trans-alkene borates can construct some special functional groups through coupling reactions, which are particularly important in organic synthesis. However, the preparation methods of trans-alkene borates are quite limited, and it is often difficult to obtain highly selective trans-alkene borates. The preparation method of existing literature report (E)-3-ethyl acrylate pina borate is as follows: [0003] [0004] The method uses ethyl propiolate and bispina boronate as r...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 唐拥军莫珊刘玉琴
Owner 成都安斯利生物医药有限公司
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