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Synthesis method of 3-hydroxy-4-((trimethylsilyl) ethynyl) methyl benzoate

A technology of trimethylsilyl and methyl benzoate, which is applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as product quality, unstable yield, products that cannot meet market demand, and difficulty in adapting to market competitiveness. The quality of recovered solvent is stable, the rate of catalytic synthesis is improved, and the effect of reducing the amount of catalyst

Active Publication Date: 2021-04-09
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Conventional 3-hydroxyl-4-((trimethylsilyl) ethynyl) methyl benzoate synthetic method is mostly with two (triphenylphosphine) palladium dichloride as catalyzer, and this catalyzer is expensive, and after reacting Not easy to recycle
In addition, the reaction time is too long, the requirements for reaction conditions are too high, the product quality and yield are unstable, the production cost is high, and the product cannot meet the existing market demand; and the production technology is difficult to be promoted, and it is difficult to adapt to the present Market Competitiveness

Method used

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  • Synthesis method of 3-hydroxy-4-((trimethylsilyl) ethynyl) methyl benzoate
  • Synthesis method of 3-hydroxy-4-((trimethylsilyl) ethynyl) methyl benzoate
  • Synthesis method of 3-hydroxy-4-((trimethylsilyl) ethynyl) methyl benzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1) Add 5g of phenol into a 50ml single-necked round bottom flask to melt it; add 0.75ml of ammonia dropwise and then add 8.86g of formaldehyde solution with a mass fraction of 37% dropwise; react at 80°C for 75 minutes; and use 0.6mol / L hydrochloric acid solution to adjust the pH value of the solution to neutral, and vacuum rotary evaporation dehydration to obtain 3.67 g of A-stage phenolic resin.

[0043] The obtained product A-stage phenolic resin is diluted with ethanol; 1g of F127 is placed in a 50ml round bottom flask and 20ml of ethanol is added to dissolve the F127, and the A-stage phenolic resin diluted with ethanol is added dropwise; the ethanol in the mixture is completely volatilized; Thermally polymerized at 100°C, and finally calcined the polymer at 350°C for 6 hours to obtain a catalyst carrier.

[0044] 2 g of the catalyst carrier was added to deionized water, and 0.2 g of palladium dichloride was added, and stirred at room temperature for 3 h to obtain a...

Embodiment 2

[0049] 1) Add 5g of phenol into a 50ml single-necked round bottom flask to melt it; add 0.75ml of ammonia dropwise and then add 8.86g of formaldehyde solution with a mass fraction of 37% dropwise; react at 80°C for 75 minutes; and use 0.6mol / L hydrochloric acid solution to adjust the pH value of the solution to neutral, and vacuum rotary evaporation dehydration to obtain 3.71 g of A-stage phenolic resin.

[0050] The obtained product A-stage phenolic resin is diluted with ethanol; 1g P123 is placed in a 50ml round-bottomed flask and 20ml of ethanol is added to dissolve P123, and the A-stage phenolic resin diluted with ethanol is added dropwise; ethanol is completely volatilized in the mixture; Thermally polymerized at 100°C, and finally calcined the polymer at 550°C for 4.5 hours to obtain a catalyst carrier.

[0051] 2 g of the catalyst carrier was added to ethanol, and 0.2 g of palladium dichloride was added, and stirred at room temperature for 3 h to obtain a palladium-supp...

Embodiment 3

[0056] 1) Add 5g of phenol into a 50ml single-necked round bottom flask to melt it; add 0.75ml of ammonia water dropwise and then add 8.86g of formaldehyde solution with a mass fraction of 37% dropwise; react at 80°C for 75 minutes; and use 0.6mol / L hydrochloric acid solution to adjust the pH value of the solution to neutral, and vacuum rotary evaporation and dehydration to obtain 3.63 g of A-stage phenolic resin.

[0057] The obtained product A-stage phenolic resin is diluted with ethanol; 1g F108 is placed in a 50ml round-bottomed flask and 20ml of ethanol is added to dissolve the F108, and the A-stage phenolic resin diluted with ethanol is added dropwise; ethanol is completely volatilized in the mixture; Thermally polymerized at 100°C, and finally calcined the polymer at 650°C for 3 hours to obtain a catalyst carrier.

[0058] Add 2 g of the catalyst carrier into methanol, and add 0.2 g of palladium dichloride, and stir at room temperature for 3 h to obtain a palladium-supp...

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Abstract

The invention relates to a synthetic method of 3-hydroxy-4-((trimethylsilyl) ethynyl) methyl benzoate, and belongs to the technical field of synthesis of medical intermediates. According to the method, 4-iodo-3-hydroxybenzoic acid and trimethylsilylacetylene are taken as raw materials, and under an alkaline system, the 3-hydroxy-4-((trimethylsilyl) ethynyl) methyl benzoate is synthesized under the catalysis of a palladium-loaded ordered mesoporous carbon catalyst and a cuprous iodide-triphenylphosphine complex. The palladium-loaded ordered mesoporous carbon catalyst used in the synthesis method is simple to synthesize and beneficial to recovery. The catalytic synthesis rate of the 3-hydroxy-4-((trimethylsilyl) ethynyl) methyl benzoate is increased, the reaction period is shortened, the synthesis yield is greatly increased and reaches 94%, and the obtained product is stable in quality and relatively high in purity.

Description

technical field [0001] The invention relates to a method for synthesizing methyl 3-hydroxy-4-((trimethylsilyl)ethynyl)benzoate, belonging to the technical field of pharmaceutical intermediate synthesis. Background technique [0002] Methyl 3-hydroxy-4-((trimethylsilyl)ethynyl)benzoate is an important pharmaceutical intermediate, mainly used in the synthesis of benzofuran-6-carboxylic acid. And benzofuran-6-carboxylic acid is the key fragment of ritazast. Ritazast is the first new LFA-1 drug, which belongs to the antagonist of leukocyte function antigen 1, and it is also the first new drug that can improve and treat the symptoms of dry eye disease. Dry eye disease is one of the most troublesome diseases for ophthalmologists, and there is an urgent need for treatment. The only other similar drug is "cyclosporine", so the clinical application of ritazast will be more extensive in the near future. It will be a strong competitor to cyclosporine-like dry eye drug Restasis. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/083Y02P20/584
Inventor 徐业岗郭凯刘淑盟
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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