Synthesis method of aryl-substituted homoallylic alcohol

A high allyl alcohol, synthetic method technology, applied in the formation/introduction of hydroxyl groups, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problems of harsh reaction conditions, limited raw material sources, expensive catalysts, etc., and achieve the reaction route The effect of short time, wide source of raw materials and cheap catalyst

Active Publication Date: 2019-04-26
CHUZHOU UNIV
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Aiming at the problems of aryl-substituted homoallylic alcohols such as long route, limited sources of raw materials, expensive catalysts, harsh reaction conditions, etc., the present invention provides a simple and cheap copper catalyst with wide raw material sources, mild reaction conditions and compatible functional groups Good performance, short reaction route, only one-step reaction based on copper-catalyzed preparation of aryl-substituted homoallylic alcohol synthesis method

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
  • Synthesis method of aryl-substituted homoallylic alcohol
  • Synthesis method of aryl-substituted homoallylic alcohol
  • Synthesis method of aryl-substituted homoallylic alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1, the reaction formula of this embodiment is as follows:

[0062]

[0063] (1) Under air, cuprous chloride (CuCl, 10mol%), tetramethylethylenediamine (TMEDA, 15mol%), lithium tert-butoxide (LiO t Bu, 2.5eq), m-methoxy-aryl neopentyl glycol boroester (2eq) were added to a sealed reaction tube with a branch tube containing magnetons, and the reaction tube was flushed with argon three times. Under the protection of argon, add 0.6mL N,N-dimethylformamide to the reaction tube, then add vinyl epoxy (0.25mmol) to the reaction solution under the protection of argon, stopper the stopper, and place at 60 °C in an oil bath and stirred for 10 hours.

[0064] (2) Quench the material obtained in step (1) by adding saturated ammonium chloride, add ethyl acetate and mix thoroughly, filter out the solid residue with a short silica gel column, and keep the organic phase.

[0065] (3) Spin dry the solvent in the organic phase obtained in step (2) to obtain a crude product...

Embodiment 2

[0067] The reaction formula of this embodiment is as follows:

[0068]

[0069] (1) Under air, cuprous chloride (CuCl, 10mol%), tetramethylethylenediamine (TMEDA, 15mol%), lithium tert-butoxide (LiO t Bu, 2.5eq), p-chloroaryl neopentyl glycol boroester (2eq) were added to a sealed reaction tube with a branch tube containing magnetons, and the reaction tube was flushed with argon three times. Under the protection of argon, add 0.6mL N,N-dimethylformamide to the reaction tube, then add vinyl epoxy (0.25mmol) to the reaction solution under the protection of argon, stopper the stopper, and place at 60 °C in an oil bath and stirred for 10 hours.

[0070] (2) Quench the material obtained in step (1) by adding saturated ammonium chloride, add ethyl acetate and mix thoroughly, filter out the solid residue with a short silica gel column, and keep the organic phase.

[0071] (3) Spin dry the solvent in the organic phase obtained in step (2) to obtain a crude product, and then purif...

Embodiment 3

[0073] The reaction formula of this embodiment is as follows:

[0074]

[0075] (1) Under air, cuprous chloride (CuCl, 10mol%), tetramethylethylenediamine (TMEDA, 15mol%), lithium tert-butoxide (LiO t Bu, 2.5eq), p-bromoaryl neopentyl glycol boroester (2eq) were added to a sealed reaction tube with a branch tube containing magnetons, and the reaction tube was flushed with argon three times. Under the protection of argon, add 0.6mL N,N-dimethylformamide to the reaction tube, then add vinyl epoxy (0.25mmol) to the reaction solution under the protection of argon, stopper the stopper, and place at 60 °C in an oil bath and stirred for 10 hours.

[0076] (2) Quench the material obtained in step (1) by adding saturated ammonium chloride, add ethyl acetate and mix thoroughly, filter out the solid residue with a short silica gel column, and keep the organic phase.

[0077] (3) Spin dry the solvent in the organic phase obtained in step (2) to obtain a crude product, and then purify...

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 relates to compound preparation, belongs to the field of organic synthesis and discloses a synthesis method of aryl-substituted homoallylic alcohol. An aryl boron compound and alkenyl epoxy serve as raw materials to react in a solvent under the action of a copper catalyst, ligands and alkali, and thus an aryl-substituted homoallylic alcohol compound with E-configuration is obtained.The aryl-substituted homoallylic alcohol synthesized through the synthesis method has the advantages of short synthetic route, high reaction yield and the like, and the problems that the route of currently synthesizing the aryl-substituted homoallylic alcohol is long, the reaction condition is harsh and the total reaction yield is low are solved. Meanwhile, the feeding mode of a reaction system issimple, a reaction reagent is stable to air and water, and actual operation is more convenient. The reaction region and stereoselectivity are high, no by-product is generated, and separation is easy.Meanwhile, the reaction can be well compatible with certain sensitive groups, and functional group compatibility is superior.

Description

technical field [0001] The invention relates to compound preparation and belongs to the field of organic synthesis. Specifically relates to a synthetic method of aryl-substituted homoallyl alcohol. Background technique [0002] Alcohol is an important class of organic compounds, which widely exist in medicine, food and other industries. And alcohol is also an important class of organic synthesis intermediates, which can be converted into organic synthons such as alkyl halides and alkyl sulfonates through simple chemical reactions, and participate in various metal-catalyzed cross-coupling reactions. Build C-C bonds and C-heterobonds. [0003] As a special kind of unsaturated hydrocarbon-containing alcohol compounds, homoallyl alcohol is a very important intermediate in organic synthesis, and homoallyl alcohol structure skeleton is required in many types of reactions. As a special class of homoallylic alcohols, aryl-substituted homoallylic alcohols have important applicatio...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/48C07C41/30C07C43/23C07C29/36C07D307/42C07B41/02
CPCC07B41/02C07C29/36C07C41/30C07D307/42C07C43/23C07C33/483
Inventor 陆晓雨李劲松王金玉
Owner CHUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap