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Green preparation method for vinyl sulfone derivative in aqueous phase

A technology of vinyl sulfone and derivatives, which is applied in the field of synthesis of vinyl sulfone derivatives to achieve a wide range of effects

Active Publication Date: 2018-10-09
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As far as the inventors know, there is no prior art report on the reaction that can prepare vinyl sulfone derivatives at room temperature in aqueous phase in a metal-free system

Method used

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  • Green preparation method for vinyl sulfone derivative in aqueous phase
  • Green preparation method for vinyl sulfone derivative in aqueous phase
  • Green preparation method for vinyl sulfone derivative in aqueous phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 compound (E)-1-methoxy group-4-(2-tosyl vinyl) benzene

[0029]

[0030] Add 4-methoxy-styrene ( 40.2mg, 0.3mmol), p-toluenesulfonyl hydrazide (67.0mg, 0.36mmol), TBAI (tetrabutylammonium iodide, 22.1mg, 0.06mmol), TBHP (tert-butanol peroxide, 32.4mg, 0.36 mmol) and solvent water (1mL), the reaction bottle was placed at 25°C under air atmosphere conditions to stir the reaction, and the reaction process was monitored by TLC or GC until the raw materials were completely reacted (reaction time 36 hours), and the reaction solution after the reaction was completed Extracted three times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product (E )-1-methoxy-4-(2-tosylvinyl)benzene. (80% yield); 1H NMR (400MHz, DMSO-d6) δ: 7...

Embodiment 2

[0032] No accelerator TBAI is added, all the other conditions are the same as in Example 1, the yield of target product (E)-1-methoxyl-4-(2-tosylvinyl)benzene is 0%, 4-methoxyl- Styrene recovery was 77%.

Embodiment 3

[0034] Substitute iodine simple substance for TBAI in embodiment 1, all the other conditions are the same as embodiment 1, through TLC or GC monitoring reaction process, to raw material reaction completely (reaction time 36 hours), the reaction solution after the reaction is completed is extracted three times with ethyl acetate , the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product (E)-1-methoxy The yield of 4-(2-tosylvinyl)benzene was 44%.

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PUM

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Abstract

The invention relates to a green preparation method for a vinyl sulfone derivative in an aqueous phase. The method comprises the following steps: putting an olefin compound (1a), a sulfonyl hydrazidecompound of formula (2a) as shown in the specification, tetrabutylammonium iodide (TBAI), tert-butyl hydroperoxide (TBHP) and solvent water into a Schlenk reaction kettle, carrying out a stirring reaction on the reaction kettle at a certain temperature and an air atmosphere, monitoring the reaction process through TLC (Thin Layer Chromatography) or GC (Gas Chromatograph) till raw materials are completely reacted, and carrying out aftertreatment, thereby obtaining a target product, namely the vinyl sulfone derivative (I) as shown in the specification.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a synthesis method of vinyl sulfone derivatives. Background technique [0002] Vinyl sulfone derivatives widely exist in drug molecules and biologically active molecules, and are widely used in medicine and biology, so they have attracted extensive and lasting attention from chemists and biologists. As a subclass of vinyl sulfone derivatives, aryl-substituted vinyl sulfone backbones are also very important structural units. More and more aryl-substituted vinyl sulfone structures have been found to be the core skeletons of many bioactive molecules and have broad application prospects. [0003] The inventors found that the synthesis pathways for the synthesis of vinyl sulfone derivatives in the prior art mainly include: the oxidation of vinyl sulfide, the Hornere-Wadsworthe-Emmons reaction of sulfonyl phosphonate and carbonyl compound, sulfonyl acetic acid and aromat...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/18C07C317/22
CPCC07C315/00C07C317/18C07C317/22
Inventor 徐旭东魏文廷高乐涵
Owner NINGBO UNIV
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