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Green preparation method of 2, 3-dihydrofuran compound

A technology of dihydrofuran and dicarbonyl compounds, which is applied in the field of organic synthesis, can solve problems such as troubles, the necessity of using alkali or oxidant as a catalyst, and high reaction temperature, and achieve a wide range of effects

Active Publication Date: 2021-01-01
NINGBO UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, from the viewpoint of eco-friendliness and practicality, these achievements are still plagued by some unfavorable factors, such as the use of catalysts, the necessity of bases or oxidants in the reaction, the need for higher reaction temperatures, or toxic organic solvents.

Method used

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  • Green preparation method of 2, 3-dihydrofuran compound
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  • Green preparation method of 2, 3-dihydrofuran compound

Examples

Experimental program
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Effect test

Embodiment 1

[0026]

[0027] In the Schlenk bottle, add the compound (55.6mg, 0.2mmol) shown in formula 1a, the halogenation reagent (54.0mg, 0.24mmol) shown in formula 2a, DMSO / H 2 O (0.5mL / 1.5mL), then the reactor was stirred and reacted at room temperature, and the reaction process was monitored by TLC until the raw material disappeared (reaction time was 8 hours). After the reaction was completed, the reaction solution was extracted with ethyl acetate, organic The 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 I-1 (95% yield); 1 H NMR (500MHz, CDCl 3 )δ: 7.37-7.36(m, 2H), 7.18-7.08(m, 4H), 7.00-6.96(m, 4H), 3.50-3.43(m, 2H), 3.25-3.14(m, 2H), 1.67( s, 3H); 13 C NMR (125MHz, CDCl 3 )δ: 193.4, 164.4, 138.9, 131.2, 130.1, 130.0, 129.3, 129.0, 127.7, 111.9, 85.2, 44.2, 26.2, 15.0.

Embodiment 2

[0029] The amount of the halogenation reagent NIS was 2.0eq (90.0mg), and the other conditions were the same as in Example 1, and the yield of the target product I-1 was 96%.

Embodiment 3

[0031] The amount of DMSO used was 0.2 mL, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 20%.

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Abstract

The invention relates to a green preparation method of a 2, 3-dihydrofuran compound from a 1, 3-dicarbonyl compound through a halogen cyclization reaction without any additive system, and the reactionis carried out in an aqueous solution at room temperature in the air. The method comprises the following steps: adding a 1, 3-dicarbonyl compound, a halogenating reagent and a solvent into a Schlenkreaction bottle, and stirring the mixture for reaction at room temperature to obtain a target product.

Description

technical field [0001] This application belongs to the field of organic synthesis, and specifically relates to a green method for preparing 2,3-dihydrofuran compounds through halogen cyclization reaction of 1,3-dicarbonyl compounds without any additive system. The reaction is carried out in an aqueous solution at room temperature. Can be carried out in the air. Background technique [0002] Undoubtedly, water with its low-cost, safe, non-toxic and environmentally friendly properties is the most attractive chemical reaction medium in the field of green and sustainable chemistry. In addition, dimethyl sulfoxide (DMSO), as a universal green solvent, provides a broader space for the development of green organic reactions. On the other hand, it is one of the most ideal methods to realize the organic reaction open in the air at room temperature, because the cost and energy consumption can be minimized. Thus, organic transformations in water / DMSO mixed media open to air at room t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/28C07D307/30
CPCC07D307/28C07D307/30
Inventor 魏文廷曹婷婷张伟康张键胡森杰
Owner NINGBO UNIV
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