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Method for synthesizing 4-aryl-4,5-dihydrofuran

A technology for dihydrofuran and derivatives, which is applied in the field of high-yield synthesis of 4-aryl-4, can solve the problems of low yield, poor substrate universality, complex synthesis process, etc., and achieve simple reaction process and low cost Low, easy-to-handle effect

Inactive Publication Date: 2010-09-08
SICHUAN UNIV
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Problems solved by technology

[0013] To sum up, most of the current preparation methods of such compounds use heavy metals as catalysts, or use multi-step reactions to achieve the synthesis of the final product. The synthesis process is relatively complicated, and the yield is generally low, and the universality of the substrate is not strong.

Method used

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  • Method for synthesizing 4-aryl-4,5-dihydrofuran
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  • Method for synthesizing 4-aryl-4,5-dihydrofuran

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Embodiment 1-3

[0040] Embodiment 1-3 mainly investigates the influence of temperature of reaction, reaction time

[0041]

Embodiment 1

[0043] With β-nitrostyrene (0.2mol) 29.8g, acetylacetone (0.4mol) 40.0g, K 2 CO 3 (0.12mol) 16.6g, DMSO (200ml), was added to a 500ml reaction flask. After stirring and reacting at 30°C for 8 hours, the conversion of the nitrostyrene raw material was complete. Dilute hydrochloric acid (1 mol / L) was added to pH = 6, extracted with ethyl acetate, washed with water and saturated brine in turn once. Dry over anhydrous sodium sulfate, evaporate ethyl acetate, and separate by flash column chromatography (petroleum ether: ethyl acetate = 8:1) to obtain the target product with a yield of 58%.

Embodiment 2

[0045] With β-nitrostyrene (0.2mol) 29.8g, acetyl lactone (0.4mol, 2eq) 40.0g, K 2 CO 3 (0.12mol, 0.6eq) 16.6g, DMSO (200ml), was added to a 500ml reaction flask, stirred and reacted at 80°C for 1 hour, and the conversion of the nitrostyrene raw material was complete. Dilute hydrochloric acid (1 mol / L) was added to pH = 6, extracted with ethyl acetate, washed with water and saturated brine in turn once. Dry over anhydrous sodium sulfate, evaporate ethyl acetate, separate by flash column chromatography (petroleum ether: ethyl acetate = 8: 1), yield 94%

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Abstract

The invention discloses a method for synthesizing 4-aryl-4,5-dihydrofuran under the catalysis of alkali, In the method aryl substituted nitroethylene and a 1,3-dicarbonyl compound taken as raw materials and dimethylsulfoxide taken as a solvent are reacted for 0.5 to 8 hours at the temperature of between 30 and 80 DEG C under the catalysis of the alkali to directly obtain the 4-aryl-4,5-dihydrofuran by a one pot method.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 4-aryl-4,5-dihydrofuran derivatives with high yield. Background technique [0002] Dihydrofuran compounds are one of the most common structural units in natural products, and are also important intermediates in organic synthesis, and are widely used in the synthesis of drugs and natural products. The existing technology mainly focuses on the preparation method of 4-aryl-4,5-dihydrofuran derivatives: [0003] (1) Take styrene as raw material and acetylacetone as raw material, synthesize 4-phenyl-4,5-dihydrofuran derivatives under the action of thallium acetate and perchloric acid, the yield is medium, but heavy metal and perchloric acid The consumption is relatively large, and the specific reaction process is as follows (Tetrahedron, 1966, 22, 407-413): [0004] [0005] (2) Take styrene as raw material and acetylacetone as raw material, synthesize 4...

Claims

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Application Information

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IPC IPC(8): C07D307/28C07D307/79C07D307/34
Inventor 余孝其李坤吴明雨王娜
Owner SICHUAN UNIV
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