Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 3-ethyl-4-methylol acetophenone

A technology of hydroxymethyl acetophenone and hydroxymethyl, applied in the field of preparing 3-ethyl-4-hydroxymethyl acetophenone, can solve the problems of difficult to realize industrialized production, high reaction cost, expensive use, etc. Easy to control, simple reaction steps, and the effect of improving yield

Inactive Publication Date: 2019-03-12
荆门医药工业技术研究院 +1
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 3-Ethyl-4-hydroxymethylacetophenone is an important intermediate for the synthesis of BAF312, and its market prospect is very promising. Currently, reports generally use 4-methylacetophenone as the starting material, ethylene trifluoroboric acid Potassium is the coupling reagent, and

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 3-ethyl-4-methylol acetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of 3-trimethylsilylethynyl-4-hydroxymethylacetophenone:

[0022] Into a 500ml three-neck flask, add 5.529g of 4-hydroxymethyl-3-bromoacetophenone, 0.23g of cuprous bromide, 0.5g of bistriphenylphosphine palladium dichloride, 15.8g of cesium carbonate, and 60mL of anhydrous tetrahydrofuran , vacuuming-nitrogen replacement for 3 times, then adding 6mL of anhydrous THF solution of trimethylsilylacetylene in batches, after dropping, heating and refluxing at 80°C for 16h, TLC monitored the completion of the reaction, the reaction liquid was cooled and filtered, and the filter cake was washed with EA About 3 times, the filtrate was collected, the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain the crude product of 3-trimethylsilylethynyl-4-hydroxymethylacetophenone, which was recrystallized from absolute ethanol 4.189 g of refined product of 3-trimethylsilylethynyl-4-hydroxymethylacetophenone was obta...

Embodiment 2

[0032] Synthesis of 3-trimethylsilylethynyl-4-hydroxymethylacetophenone:

[0033] Into a 500ml three-necked flask, 20g of 4-hydroxymethyl-3-bromoacetophenone, 0.84g of cuprous bromide, 1.8g of bistriphenylphosphine palladium dichloride, 57.2g of cesium carbonate, and 200mL of anhydrous tetrahydrofuran were successively added. Vacuumize and replace with nitrogen for 3 times, then add 43mL of anhydrous THF solution of triisopropylsilylacetylene in batches, after dropping, heat and reflux at 80°C for 16h, monitor the completion of the reaction by TLC, suction filter the reaction solution after cooling, and wash the filter cake with EA About 3 times, the filtrate was collected, the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain the crude product of 3-trimethylsilylethynyl-4-hydroxymethylacetophenone, which was recrystallized from absolute ethanol 16.2 g of refined product of 3-trimethylsilylethynyl-4-hydroxymethyla...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing 3-ethyl-4-methylol acetophenone. The method includes steps of S1, carrying out coupling reaction on 4-methylol-3-bromoacetophenone and trimethylsilylacetylene or ethynyltriisopropylsilane to generate 3-trimethyl silicon acetenyl-4-methylol acetophenone; S2, hydrolyzing the 3-trimethyl silicon acetenyl-4-methylol acetophenone under alkaline conditionsto generate 3-acetenyl-4-methylol acetophenone; S3, carrying out reduction on the 3-acetenyl-4-methylol acetophenone under the conditions of hydrogen, palladium and carbon to obtain the 3-ethyl-4-methylol acetophenone. The method has the advantages that the yield of the 3-ethyl-4-methylol acetophenone can be greatly increased, the highest yield of the 3-ethyl-4-methylol acetophenone can reach 55%at least, the method includes simple reaction steps and is easy to control, and reaction procedures are mild.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a method for preparing 3-ethyl-4-hydroxymethylacetophenone. Background technique [0002] BAF312 (Siponimod), the Chinese name is Siponimod, as a new generation of immunomodulatory drug, it has been successful in phase III clinical study EXPAND, and the drug has broad application prospects in the future. [0003] BAF312 is a next-generation selective sphingosine-1-phosphate (S1P) receptor modulator, which is normally found on the surface of specific cells in the central nervous system (CNS) and is responsible for the loss-of-function that drives multiple sclerosis (SPMS) CNS injury. BAF312 can enter the brain, prevent the activation of these harmful cells by binding to specific receptors, and help reduce the loss of physical and cognitive functions associated with SPMS. Its structural formula is as follows: [0004] [0005] 3-Ethyl-4-hydroxymethylacetophenone is an importan...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C45/62C07C49/84
CPCC07C45/61C07C45/62C07F7/0827C07C49/84
Inventor 严少康李立威许方亮毛学荣廖春花
Owner 荆门医药工业技术研究院
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com