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Novel cis-styryl benzofuranone compound and efficient synthesis method thereof
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A technology of styrylbenzene and a synthesis method, applied in directions such as organic chemistry, chemical recovery, etc., can solve problems such as less reports on synthesis techniques, and achieve the effects of high yield of target product, low cost, and simple and convenient reaction operation.
Pending Publication Date: 2022-08-02
HUNAN UNIV
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1,2 Using benzofuranone and phenylacetylene as starting materials, CuCl as catalyst, di-tert-butyl peroxide as oxidant, and nitrogen gas to synthesize olefins in one pot, the method has easy-to-obtain raw materials, simple operation, no solvent, The reaction conditions are relatively mild, the product yield and purity are high, and there are few reports on its synthesis process
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example 1
[0015] In a 10 mL reaction tube, add the benzofuranone derivative I (R 1 =4-methyl, R 2 =H)0.2mmol, phenylacetylene derivative II(R 3 =4-methoxy) 0.2 mmol, cuprous chloride 0.01 mmol, di-tert-butyl peroxide 0.4 mmol, and the reaction was stirred at 100° C. for 3 h. After the reaction, the target compound III (R) was obtained by column chromatography. 1 =4-methyl, R 2 =H,R 3 =4-methoxy) to give a white powder in 97% yield.
[0016] Characterization data: 1 H NMR (400MHz, DMSO-d 6 )δ7.38-7.29(m,3H),7.22(t,J=8.9Hz,3H),7.13(d,J=8.2Hz,1H),7.09(s,1H),6.83(d,J=11.8 Hz, 1H), 6.65(s, 4H), 6.12(d, J=11.8Hz, 1H), 3.68(s, 3H), 2.27(s, 3H). 13 C{ 1 H}NMR(101MHz,DMSO-d 6 )δ175.9,158.8,150.3,141.2, 134.5,133.8,131.9,130.4,130.2,129.6,129.4,128.4,128.4,127.0,126.2,113.6,111.0,56.7,55.5,21.0.HRMS(EIm / z) M + ]calcd for C 24 H 20 O 3 356.1412,Found 356.1419.
example 2
[0018] In a 10 mL reaction tube, add the benzofuranone derivative I (R 1 =4-methyl, R 2 =H)0.2mmol, phenylacetylene derivative II(R 3 =4-methoxy) 0.2 mmol, di-tert-butyl peroxide 0.4 mmol, and the reaction was stirred at 100° C. for 3 h. After the reaction, there was no target product.
example 3
[0020] In a 10 mL reaction tube, add the benzofuranone derivative I (R 1 =4-methyl, R 2 =H)0.2mmol, phenylacetylene derivative II(R 3 =4-methoxy) 0.2 mmol, cuprous chloride 0.01 mmol, and the reaction was stirred at 100° C. for 3 h. After the reaction, there was no target product.
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Abstract
According to the method, benzofuranone, phenylacetylene and derivatives thereof are used as raw materials, cuprous chloride is used as a catalyst, and di-tert-butyl peroxide is used as an oxidant in the absence of a solvent, so that the cis-styryl benzofuranone compound is synthesized. The cis-styryl benzofuranone compound is obtained with high yield, the reaction time is prolonged, and the main product is a diene compound. The styrene compound can be converted into a benzopyran compound. The method has the advantages of low cost, high yield, simplicity and convenience in operation, no pollution and the like, and has a potential industrial application prospect. The method provides a cheap and green way for the preparation of the cis-styryl benzofuranone compound.
Description
【Technical field】 [0001] The invention relates to a novel cis-styryl benzofuranone compound and a new efficient synthesis method thereof, belonging to the field of organic synthesis. The reaction process conditions are simple and the yield is good, and the benzofuranone is alkenylated into a styrene compound by using a copper catalyst. The reaction time is prolonged, and the main product is a diene compound. Styrene compounds can be converted into benzopyrans under the promotion of sodiummethoxide. 【Background technique】 [0002] Olefins are important fine chemical intermediates, which can be widely used in the fields of pesticides, organic functional materials and medicine. The main methods for the synthesis of complex olefins include Heck reaction, Wittig reaction and elimination reaction and so on. However, these reactions all have certain disadvantages, such as the Heck reaction requires the use of expensive palladium catalysts, and the reaction efficiency and stereo...
Claims
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