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Method for removing methyl protecting group from phenolic hydroxyl under mild condition

A technology of phenolic hydroxyl methyl group and protecting group, applied in the field of organic synthesis, can solve the problems of difficult reaction process, difficult preservation of reagents, high price, etc., and achieve the effects of effective specific structure, mild conditions and few side reactions.

Inactive Publication Date: 2016-06-15
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These reagents have the following disadvantages: the reagents are not easy to store, easy to be damp, expensive, relatively violent reaction, difficult to control the reaction process, etc., so it is necessary to find a mild reagent for deprotection

Method used

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  • Method for removing methyl protecting group from phenolic hydroxyl under mild condition
  • Method for removing methyl protecting group from phenolic hydroxyl under mild condition
  • Method for removing methyl protecting group from phenolic hydroxyl under mild condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014]

[0015] 1mmol (0.22g) 2-methoxy-N 1 ,N 3 - Dimethylisophthalimide and 2mmol (0.64g) tetrabutylammonium bromide were placed in a 50ml round-bottomed flask, vacuumed, replaced with nitrogen, then added 10ml of dry tetrahydrofuran, stirred, and heated To 70 °C, TLC trace spot plate. After the reaction was completed, 1M hydrochloric acid was added to the reaction flask to quench. Add an appropriate amount of saturated saline and dichloromethane, extract and separate the liquids, combine the organic phases, dry over anhydrous sodium sulfate, and spin dry under reduced pressure. The residue is quickly separated by column chromatography to obtain 0.19 g of the product, with a yield of 91%.

Embodiment 2

[0017] 1mmol (0.22g) 2-methoxy-N 1 ,N 3 - Dissolve dimethylisophthalimide in tetrahydrofuran, then add tetrabutylammonium bromide, heat and stir, and react at 70 degrees Celsius for 10 hours. After the reaction, add 1M hydrochloric acid to the reaction bottle to quench . Add an appropriate amount of saturated saline and dichloromethane, extract and separate the liquids, combine the organic phases, dry with anhydrous sodium sulfate, and spin dry under reduced pressure. The residue is quickly separated by column chromatography to obtain 0.185 g of the product, with a yield of 89%.

Embodiment 3

[0019] 1mmol (0.22g) 2-methoxy-N 1 ,N 3 - Dissolve dimethylisophthalimide in 10ml tetrahydrofuran, then add 2mmol (0.64g) tetrabutylammonium bromide, heat and stir, and react at 70 degrees Celsius for 10 hours. Add 1M hydrochloric acid to quench. Add an appropriate amount of saturated saline and dichloromethane, extract and separate the liquids, combine the organic phases, dry over anhydrous sodium sulfate, and spin dry under reduced pressure. The residue is quickly separated by column chromatography to obtain 0.185 g of the product, with a yield of 89%.

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Abstract

The invention discloses a method for removing a methyl protecting group from a phenolic hydroxyl under a mild condition. The method is characterized in that a methyl of the phenolic hydroxyl with the amide structure can be completely removed by taking TBACl (Tetrabutylammonium Chloride), TBABr (Tetrabutylammonium Bromide) or TBAI (Tetrabutylammonium Iodide) as a removal agent for the methyl of the phenolic hydroxyl with an amide structure and tetrahydrofuran as a solvent and stirring for four hours at 70 DEG C. The method disclosed by the invention is mild in reaction conditions, less in byproducts, high in yield and simple in operation, and is capable of selectively removing the methyl protecting group of the phenolic hydroxyl with a specific structure.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for removing a phenolic hydroxymethyl protecting group under mild conditions. Background technique [0002] In organic synthesis, the phenolic hydroxyl group is an important functional group, which itself has functionality or can be converted into other functional groups through chemical reactions. Since the phenolic hydroxyl group is relatively active, it is necessary to use protecting groups to Its protection prevents it from reacting with oxidizing agents, electrophiles or a nucleophilic phenolic oxygen ion and even weak alkylating agents and acylating agents, and finally removes the protecting group at an appropriate time. In protecting group chemistry, methyl ether group is the most commonly used protecting group for phenolic hydroxyl groups, because methyl ether group is not only easy to prepare, but also stable to a series of reagents. [0003] Since phenol methy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C235/60
CPCY02P20/55C07C231/12C07C235/60
Inventor 秦波黄露贾子悦师晓云朱素珍王鹏
Owner CHONGQING UNIV
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