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

Composition for preparing propargyl ether

A technology of propargyl ether and composition, applied in the field of preparing propargyl ether composition, can solve problems such as high toxicity, increased reaction cost, operator injury and the like

Active Publication Date: 2018-11-02
SICHUAN UNIV
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned Nicholas reaction is widely used for the preparation of propargyl ethers, but it suffers from an obvious drawback: a stoichiometric amount of catalyst Co 2 (CO) 8 , not only expensive, increased reaction costs, but also highly toxic, causing harm to operators and unfriendly to the environment

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
  • Composition for preparing propargyl ether
  • Composition for preparing propargyl ether
  • Composition for preparing propargyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0132] Embodiment 1 The preparation method of propargyl ether of the present invention

[0133]

[0134] In a nitrogen-filled glove box, the Et 3 N (56 μL, 0.40 mmol, 2.0 equiv), boric acid B1 (2.0 mg, 0.010 mmol, 5.0 mol%), fatty alcohol (0.24 mmol, 1.2 equiv) and THF (0.3 mL) were sequentially added to a screw cap vial (vial A) . Cap vial A tightly and take it out of the glove box.

[0135] In a nitrogen-filled glove box, the Cu(CH 3 EN) 4 BF 4 (3.2mg, 0.010mmol, 5.0mol%), Ligand L5 (4.8mg, 0.020mmol, 10mol%) and THF (0.2mL) were sequentially added to another screw cap vial (vial B) with a magnetic stir bar . Vial B was stirred at 60 °C for 1 h, cooled to room temperature, and propargyl ester (0.20 mmol, 1.0 equiv) was added. After the vial B was tightly capped, it was taken out of the glove box, stirred at room temperature for 10 min, and cooled to -20°C. At this temperature, the solution in vial A was added to vial B via an airtight syringe, and the resulting re...

Embodiment 2

[0137] Example 2 The universality of the composition of the present invention for the preparation of propargyl ether

[0138]

[0139] a, the universality of propargyl compounds (with the above-mentioned compound 11 as fatty alcohol substrate):

[0140]

[0141] b, the universality of fatty alcohols (with the above-mentioned compound 10 as the propargyl substrate):

[0142]

[0143] Note: Unless otherwise specified, the reactions in the examples were carried out on a 0.2 mmol scale, Cu(CH 3 EN) 4 BF 4 (5mol%), L5 (10mol%), B1 (5mol%), Et 3 N(2equiv), reacted at -20°C for 24h. The yield is the separation yield, the ee value is detected by HPLC, and the dr value is detected by the crude NMR of the reaction solution 1 H NMR determination. [a] Ligand L6 is used.

[0144] Above-mentioned reaction result proves the universality of propargyl ether preparation method of the present invention: 1, with respect to propargyl base substrate, aromatic ring is (10a-b, 10g) of...

Embodiment 3

[0145] Example 3 The composition of the present invention is used for the regioselective propargylation of carbohydrate derivatives

[0146] Sugar is an extremely important class of chemical structural units. Sugar is not only a necessary group for the function of glycoproteins and glycolipids, but also an important component of many natural drug molecules. For a long time, the research on sugars has provided many means for human beings to understand nature, and has also produced many important marketed drugs.

[0147] The selective introduction of terminal alkynes into sugar compounds will provide great convenience for sugar research. Because, the terminal alkyne is a functional group that can participate in "click chemistry". The role of "click chemistry" in the field of sugar research has long been confirmed. At the same time, the terminal alkyne itself is also a functional group that can be easily derivatized, and can easily synthesize various derivatives of sugars. In...

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 composition for preparing propargyl ether. The composition comprises the following components: a boron compound, a copper compound, a ligand and alkali. According to the composition, copper catalyzing propargyl substitution reaction and boron catalyzing fatty alcohol activating technology are combined for the first time to successfully realize efficient preparation of propargyl ether. The composition has a good application prospect.

Description

technical field [0001] The invention relates to a composition for preparing propargyl ether, which belongs to the field of chemical synthesis. Background technique [0002] Propargyl ether is widely used in organic synthesis and is a very important intermediate in organic synthesis. Since the terminal alkyne itself is a functional group that can be easily derivatized, various derivatives can often be synthesized conveniently through propargyl ethers. In addition, terminal alkynes are important functional groups for bioorthogonal reactions and can also be used in Raman spectroscopy. [0003] Currently, propargyl ethers are usually prepared by substitution of propargyl alcohols with nucleophiles under transition metal catalyzed conditions. For example, Nicholas et al. reported an efficient method to achieve propargylation in the presence of cobalt complexing cations: propargyl alcohol with Co 2 (CO) 8 Form Co first 2 (CO) 6 The propargyl alcohol complex, then forms a car...

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): B01J31/18B01J31/30B01J31/28B01J31/02C07C41/16C07C43/166C07C43/178C07C43/176C07C269/06C07C271/44C07C253/30C07C255/54C07D209/12C07D307/42C07D333/16C07D213/30C07C43/196C07D207/12C07H23/00C07H5/10C07H7/04C07H17/04
CPCB01J31/0272B01J31/1815B01J31/28B01J31/30C07B2200/07C07C41/16C07C43/166C07C43/176C07C43/1785C07C43/1788C07C43/196C07C253/30C07C255/54C07C269/06C07C271/44C07D207/12C07D209/12C07D213/30C07D307/42C07D333/16C07H5/10C07H7/04C07H17/04C07H23/00
Inventor 钮大文张霞
Owner SICHUAN UNIV
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