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Method for preparing alcohol through exogenous alkali-free Suzuki reaction

A reaction and exogenous technology, which is applied in the preparation of carboxynitrile, carboxylate, and carbon-based compounds, can solve the problems of reagent waste, functional group compatibility check, and high synthesis cost, and achieve good compatibility and side effects. The effect of less reaction and easy raw materials

Active Publication Date: 2020-01-24
CHUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This brings problems such as high synthesis cost, waste of reagents, and compatibility check of functional groups.

Method used

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  • Method for preparing alcohol through exogenous alkali-free Suzuki reaction
  • Method for preparing alcohol through exogenous alkali-free Suzuki reaction
  • Method for preparing alcohol through exogenous alkali-free Suzuki reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The reaction of this example is as follows:

[0024]

[0025] (1) In air, nickel(II) bromide (10mol%), 4,4'-di-tert-butyl-2,2'bipyridine (12 mol%), sodium iodide (50mol%) are added to one In a sealed reaction tube with a branch tube and containing magnets, the reaction tube is flushed with argon three times. Under the protection of argon, add 0.8mL ethanol to the reaction tube, and then add phenylboronic acid (0.5mmol) and epoxycyclohexane (0.25mmol) to the reaction solution in sequence under the protection of argon. The reaction was stirred in an oil bath at 70°C for 12 hours.

[0026] (2) Add ethyl acetate to the materials obtained in step (1) and mix thoroughly, filter out the solid residue with a short silica gel column, and retain the organic phase. The solvent in the organic phase was spin-dried to obtain a crude product, which was then purified by a silica gel column. The separation yield is 85%, and the product purity is 100%

Embodiment 2

[0028] The reaction formula of this embodiment is as follows:

[0029]

[0030] (1) In air, nickel(II) bromide (10mol%), 4,4'-di-tert-butyl-2,2'bipyridine (12 mol%), sodium iodide (50mol%) are added to one In a sealed reaction tube with a branch tube and containing magnets, the reaction tube is flushed with argon three times. Under the protection of argon, add 0.8mL ethanol to the reaction tube, and then add 3-acetylphenylboronic acid (0.5mmol) and epoxycyclohexane (0.25mmol) to the reaction solution in sequence under the protection of argon. The piston was placed in a 70°C oil bath and stirred for 12 hours.

[0031] (2) Add ethyl acetate to the materials obtained in step (1) and mix thoroughly, filter out the solid residue with a short silica gel column, and retain the organic phase. The solvent in the organic phase was spin-dried to obtain a crude product, which was then purified by a silica gel column. The separation yield is 81%, and the product purity is 100%

Embodiment 3

[0033] The reaction formula of this embodiment is as follows:

[0034]

[0035] (1) In air, nickel(II) bromide (10mol%), 4,4'-di-tert-butyl-2,2'bipyridine (12 mol%), sodium iodide (50mol%) are added to one In a sealed reaction tube with a branch tube and containing magnets, the reaction tube is flushed with argon three times. Under the protection of argon, add 0.8mL ethanol to the reaction tube, and then add 3-methoxycarbonylphenylboronic acid (0.5mmol) and epoxycyclohexane (0.25mmol) to the reaction solution in sequence under the protection of argon. Tighten the piston and place it in a 70°C oil bath with stirring for 12 hours.

[0036] (2) Add ethyl acetate to the materials obtained in step (1) and mix thoroughly, filter out the solid residue with a short silica gel column, and retain the organic phase. The solvent in the organic phase was spin-dried to obtain a crude product, which was then purified by a silica gel column. The separation yield is 80%, and the product purity i...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to an alcohol compound preparation method of. In the prior art, the method for preparing the alcohol compound through the Suzuki type ring-opening coupling reaction of ternary epoxy has the following disadvantages that the substrate type is limited, the excessive lithium tert-butoxide with strong alkalinityneeds to be added in the reaction, and the like. Based on the disadvantages in the prior art, the synthesis method for preparing an alcohol compound through a Suzuki reaction, wherein the method is efficient, convenient, free of exogenous alkali and has excellent functional group compatibility. According to the invention, an epoxy compound and arylboronic acid are used as raw materials and reactwith a solvent under the conditions of a nickel catalyst and a ligand to obtain the alcohol compound; the method has advantages of mild reaction conditions, avoidance of use of exogenous alkali, highyield, few side reactions, convenience in operation and wide substrate types; and the reaction system is convenient to feed, raw materials are easy to prepare, functional group compatibility is good,and the efficient, practical and economical synthesis method is provided for synthesis of alcohol compounds.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis. Specifically, it relates to a method for preparing alcohol compounds. Background technique [0002] The transition metal-catalyzed Suzuki reaction occupies an important position in organic and pharmaceutical synthesis, and provides a synthesis method for a large number of active and drug molecules. Therefore, the Suzuki reaction won the Nobel Prize in 2010. Almost all Suzuki reactions require the addition of a chemical equivalent of an exogenous base, which leads to waste of synthesis and problems of compatibility of functional groups. [0003] Alcohol compounds are important organic structures, which are widely present in various types of active molecules. Therefore, the synthesis of alcohol compounds has always been the focus of research. Ternary epoxy compounds can undergo nucleophilic and ring-opening reactions with nucleophiles to obtain alcohol compounds. Therefore, ternary epoxy com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/36C07C35/21C07C33/20C07C45/68C07C49/83C07C67/343C07C69/76C07C253/30C07C255/53C07D211/48
CPCC07C29/36C07C45/68C07C67/343C07C253/30C07D211/48C07C2601/14C07C35/21C07C33/20C07C49/83C07C69/76C07C255/53
Inventor 陆晓雨李劲松周海嫔
Owner CHUZHOU UNIV
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