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Preparation method of 4-tosylester-2H-chromene

A technology of p-toluenesulfonic acid ester and p-toluenesulfonic acid is applied in the field of preparation of 4-p-toluenesulfonic acid ester-2H-chromene, and can solve the problems of poor atom economy, increased side reactions, unenvironmental protection, etc. The effect of short time, easy operation and less pollution

Inactive Publication Date: 2019-01-18
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the 4-p-toluenesulfonate-2 obtained by this method H - Chromene needs to be synthesized through multi-step reactions, and each step needs to be reacted in a strong base or strong acid and high temperature system, which increases the side reactions of the entire reaction, poor atom economy, environmental protection, and low yield
[0003] Development of a novel, atom-economical, and green synthetic strategy for the synthesis of 4-p-toluenesulfonate-2 H -Chromene appears to be particularly important. So far, 4-p-toluenesulfonate-2 H - Chromene has not been reported, which is a breakthrough in the traditional synthesis of alkenyl sulfonate derivatives

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: Preparation of 2,2-diphenyl 4-p-toluenesulfonate-2H-chromene

[0017] ,

[0018] A representative implementation process: Add o-propargyl phenol to the reaction flask in sequence at room temperature -1 (1.5 g, 5 mmol) and 20 ml of dry 1,4-dioxane, then p-toluenesulfonic acid ( p -TsOH, 10mmol) was added into the reaction flask, and then the reaction was placed at 60°C for 1 hour. TLC tracks the progress of the reaction. After the reaction is over, add the reaction solution to saturated sodium bicarbonate solution, then add ethyl acetate, stir well and let it stand for stratification; the separated aqueous layer is extracted with ethyl acetate, and the extracted ethyl acetate The product and the separated organic layer were combined and washed with saturated brine and dried over anhydrous sodium sulfate; the ethyl acetate solvent was evaporated, and then separated and purified by silica gel column chromatography to obtain 2,2-diphenyl 4-p-toluene Sulf...

Embodiment 2

[0020] Example 2: Preparation of 2,2-bis(p-methylphenyl)-4-p-toluenesulfonate-2H-chromene

[0021] ,

[0022] At room temperature, add o-propargyl phenol to the reaction flask in turn -2 (1.64 g, 5 mmol) and 20 ml of dry 1,4-dioxane, then p-toluenesulfonic acid ( p -TsOH, 10mmol) was added into the reaction flask, and then the reaction was placed at 60°C for 1 hour. TLC followed the progress of the reaction. The separation and purification steps were the same as in Example 1 to obtain 1.73 g of 2,2-bis(p-methylphenyl)-4-p-toluenesulfonate-2H-chromene, with a reaction yield of 72%.

[0023] Yellow solid, mp: 114-116°C. 1 H NMR (400 MHz, CDCl 3 ): δ 2.32 (s, 6 H), 2.38 (s, 3 H), 5.90 (s, 1 H), 6.73 – 6.77 (m, 1 H), 6.84 – 6.86 (m, 1 H), 7.05 –7.07 (m, 1H), 7.10 – 7.13 (m, 5H), 7.19 – 7.25 (m, 6H), 7.76 – 7.78 (m, 2H), . 13 C NMR (100 MHz, CDCl 3 ): δ 21.1, 21.7, 83.9, 116.5, 117.3, 121.0,122.2, 126.8, 128.5, 128.8, 129.8, 130.8, 137.5, 141.2, 141.7, 145.4, 153.3. HRMS...

Embodiment 3

[0024] Example 3: Preparation of 2,2-bis(p-fluorophenyl)-4-p-toluenesulfonate-2H-chromene

[0025] ,

[0026] At room temperature, add o-propargyl phenol to the reaction flask in turn -3 (1.68 g, 5 mmol) and 20 ml of dry 1,4-dioxane, then p-toluenesulfonic acid ( p -TsOH, 10mmol) was added into the reaction flask, and then the reaction was placed at 60°C for 1 hour. TLC followed the progress of the reaction. The separation and purification steps were the same as in Example 1 to obtain 1.64 g of 2,2-bis(p-fluorophenyl)-4-p-toluenesulfonate-2H-chromene, with a reaction yield of 67%.

[0027] Yellow solid, mp: 89 - 91°C. 1 H NMR (400 MHz, CDCl 3 ): δ 2.39 (s, 3 H),5.89 (s, 2 H), 6.77 – 6.81 (m, 1 H), 6.84 – 6.86 (m, 1 H), 6.97 – 7.02 (m, 4H), 7.06 – 7.08 (m, 1H), 7.11 – 7.14 (m, 1H), 7.16 –7.25 (m, 2H), 7.28 –7.32 (m, 4H),. 7.77 – 7.78 (m, 2H), 13 C NMR (100 MHz, CDCl 3): Δ 21.6, 83.2,115.0, 115.2, 116.4, 116.5, 117.2, 121.4, 122.4, 128.7, 129.8, 131.1.132.3, 139.6, 14...

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Abstract

The invention discloses a preparation method of 4-tosylester-2H-chromene, wherein ortho propargyl alcohol phenol is used as a raw material, an organic solvent is added to dissolve fully at room temperature, and then p-toluenesulfonic acid (p-TsOH) is added and reacted at 60 DEG C for 1 to 2 hours. After the reaction is completed, the reaction product is separated and purified by column chromatography on silica gel to obtain the 4-tosylester-2H-chromene. The invention has the characteristics of simple and easily accessible raw materials, mild reaction conditions, simple operation, short reaction time and less pollution and the like, and is a better chemical synthesis method with popularization and application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 4-p-toluenesulfonate-2H-chromene. Background technique [0002] 4-p-toluenesulfonate-2 H -Chromene is a relatively new type of drug intermediate, and there are few relevant literature reports. At present, 4-flavanone is mainly used to react with p-toluenesulfonic anhydride under the promotion of a strong base to obtain 4-p-toluenesulfonate-2 H - chromene. But the 4-p-toluenesulfonate-2 obtained by this method H - Chromene needs to be synthesized through multi-step reactions, and each step needs to be reacted in a strong base or strong acid and high temperature system, which increases the side reactions of the entire reaction, poor atom economy, environmental protection, and low yield. [0003] Development of a novel, atom-economical, and green synthetic strategy for the synthesis of 4-p-toluenesulfonate-2 H -Chromene appears to be...

Claims

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Application Information

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IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 肖强宋贤荣李忍
Owner JIANGXI SCI & TECH NORMAL UNIV
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