Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for synthesizing 2-aryl acrolein diacetal through palladium-catalyzed Suzuki coupling reaction

A technology of aryl acrolein diacetal and acrolein diethyl acetal, which is applied in the field of palladium-catalyzed Suzuki coupling reaction to synthesize 2-aryl acrolein diacetal, which can solve the problem of high reactivity and difficult separation isomerization Addition products, inconvenient storage and other problems, to achieve the effect of mild and efficient reaction conditions, a wide range of substrates, and good functional group compatibility

Inactive Publication Date: 2020-07-17
ZHEJIANG PHARMA COLLEGE
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have their own limitations: the substrates of the Wittig reaction have a wide range of applications, but the reaction is significantly affected by steric hindrance; the addition reaction of alkyne aldehydes needs to use expensive and poorly stable iodohydrocarbons as the source of aryl groups, and the reaction is still difficult. There are isomerization addition products that are difficult to separate; the Mizoroki-Heck reaction of propylene acetal requires the use of aryl triflate with high reactivity and inconvenient storage; 2-aryl-1,1-dichloro The ring-opening reaction of cyclopropane is limited by the substrate source

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 synthesizing 2-aryl acrolein diacetal through palladium-catalyzed Suzuki coupling reaction
  • Method for synthesizing 2-aryl acrolein diacetal through palladium-catalyzed Suzuki coupling reaction
  • Method for synthesizing 2-aryl acrolein diacetal through palladium-catalyzed Suzuki coupling reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add a stir bar to the reaction tube (10mL), weigh in Pd(OAc) 2 0.004mmol, XPhos 0.008mmol, Cs 2 CO 3 1.0mmol and 0.4mmol of 4-methoxyphenylboronic acid, vacuumize, fill with nitrogen protection, and inject 1mL of dioxane and 0.2mmol of 2-bromoacrolein diethyl acetal. The reaction tube was placed at 40°C for 3 h to complete the reaction, the reaction solution was diluted with 2 mL of ethyl acetate and 5 mL of saturated brine, and then extracted 4 times with ethyl acetate (4x5 mL); the organic phases were combined and dried over anhydrous magnesium sulfate. After filtering, the organic phase solution was removed by a rotary evaporator to remove the solvent; then the mixed solution of petroleum ether and ethyl acetate with a volume ratio of 40:1 was used as an eluent for column chromatography separation, and finally 2- (4-methoxyphenyl)acrolein diethyl acetal 40.6 mg, yield 86%, colorless liquid. The analysis data is as follows:

[0024] 1 H NMR (500MHz, CDCl 3 )δ:...

Embodiment 2

[0026] Add a stir bar to the reaction tube (10mL), weigh in Pd(OAc) 2 0.004mmol, XPhos 0.008mmol, Cs 2 CO 3 1.0mmol and 0.4mmol of 4-fluorophenylboronic acid, vacuumize, fill with nitrogen protection, and inject 1mL of dioxane and 0.2mmol of 2-bromoacrolein diethyl acetal. The reaction tube was placed at 40°C for 3 h to complete the reaction, the reaction solution was diluted with 2 mL of ethyl acetate and 5 mL of saturated brine, and then extracted 4 times with ethyl acetate (4x5 mL); the organic phases were combined and dried over anhydrous magnesium sulfate. After filtering, the organic phase solution was removed by a rotary evaporator to remove the solvent; then the mixed solution of petroleum ether and ethyl acetate with a volume ratio of 40:1 was used as an eluent for column chromatography separation, and finally 2- (4-fluorophenyl)acrolein diethyl acetal 36.3 mg, yield 81%, colorless liquid. The analysis data is as follows:

[0027] 1 H NMR (500MHz, CDCl 3 )δ:7....

Embodiment 3

[0029] Add a stir bar to the reaction tube (10mL), weigh in Pd(OAc) 2 0.004mmol, XPhos 0.008mmol, Cs 2 CO 3 1.0mmol and 0.4mmol of 2-naphthylboronic acid, vacuumize, fill with nitrogen protection, and inject 1mL of dioxane and 0.2mmol of 2-bromoacrolein diethyl acetal. The reaction tube was placed at 40°C for 3 h to complete the reaction, the reaction solution was diluted with 2 mL of ethyl acetate and 5 mL of saturated brine, and then extracted 4 times with ethyl acetate (4x5 mL); the organic phases were combined and dried over anhydrous magnesium sulfate. After filtering, the organic phase solution was removed by a rotary evaporator to remove the solvent; then the mixed solution of petroleum ether and ethyl acetate with a volume ratio of 40:1 was used as an eluent for column chromatography separation, and finally 2- (2-Naphthyl)acrolein diethyl acetal 40.4 mg, yield 79%, colorless liquid. The analysis data is as follows:

[0030] 1 H NMR (500MHz, CDCl 3 )δ:8.08-8.06(...

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 synthesizing 2-aryl acrolein diacetal through palladium catalyzed Suzuki coupling reaction, which comprises the following specific steps: adding Pd (OAc) 2, XPhos,Cs2CO3 and arylboronic acid into a reaction tube with a stirrer, vacuumizing, exchanging nitrogen, and injecting dioxane and 2-bromoacrolein diacetal; reacting at 40-60 DEG C for 3-6 hours, dilutingthe reaction solution with ethyl acetate and saturated edible salt water, and extracting with ethyl acetate; the invention provides a method for synthesizing 2-aryl acrolein diacetal through palladium-catalyzed Suzuki coupling reaction, and the method is wide in substrate application range, good in functional group compatibility and mild and efficient in reaction condition.

Description

technical field [0001] The invention relates to a method for synthesizing 2-aryl acrolein diacetal by palladium-catalyzed Suzuki coupling reaction of 2-bromoacrolein diethyl acetal. Background technique [0002] Acrolein is the simplest unsaturated olefinic aldehyde, so 2-aryl acrolein diacetal after 2-aryl acrolein protection is also widely used in organic synthesis, and is an important class of organic synthesis intermediate compounds. Realize a variety of functional group conversion reactions, such as catalytic hydrogenation of double bonds, ene hydrogenation addition reactions, carbonylation reactions and cyclization reactions, etc., as well as deprotection reactions of acetals, etc., 2-aryl acrolein diacetal Examples of derivatization reactions are as follows: [0003] [0004] At present, the general synthesis methods of 2-substituted acrolein diacetals reported in the literature mainly include Wittig reaction, intermolecular Mizoroki-Heck reaction, addition reacti...

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): C07C43/315C07C43/313C07C43/303C07C41/48C07D307/46
CPCC07C41/48C07D307/46C07C2531/22C07C43/315C07C43/313C07C43/303
Inventor 张莉周俊慧戴静波王叶毛杰
Owner ZHEJIANG PHARMA COLLEGE
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com