CN115197180B - Synthesis method of 3-selenofurans compound promoted by visible light - Google Patents

Synthesis method of 3-selenofurans compound promoted by visible light Download PDF

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CN115197180B
CN115197180B CN202210439256.7A CN202210439256A CN115197180B CN 115197180 B CN115197180 B CN 115197180B CN 202210439256 A CN202210439256 A CN 202210439256A CN 115197180 B CN115197180 B CN 115197180B
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selenofuran
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CN115197180A (en
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刘功清
王永浩
凌勇
周晨凡
姜有琴
张云倩
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Nantong University
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Abstract

The invention relates to the technical field of organic synthetic chemistry, in particular to a method for synthesizing a 3-selenofuran compound promoted by visible light. According to the invention, high propargyl alcohol and diselenide are used as reaction raw materials, and under the condition of room temperature, cyclization/selenization series reaction is carried out by irradiation of visible light to obtain the 3-selenofuran compound. The invention realizes the preparation of the 3-selenofuran compound from the homopropargyl alcohol derivative in the presence of no light catalyst for the first time; the invention does not need to use transition metal and chemical oxidant, and has the advantages of green environmental protection and the like; the invention also has the advantages of mild reaction condition, low cost, little environmental pollution, high yield, good compatibility of functional groups and the like, and has good application potential and research value.

Description

Synthesis method of 3-selenofurans compound promoted by visible light
Technical Field
The invention relates to the technical field of organic synthetic chemistry, in particular to a method for synthesizing a 3-selenofuran compound promoted by visible light.
Background
Furan is an important class of organic aromatic heterocyclic compounds whose structure is found in many natural products, drugs and bioactive molecules, exhibiting a variety of different physiological activities ((a) org.chem.front.,2021,8,2608-2642.; (b) int.j.rev.life sci.,2012,2,7-16.; (b) j.food biochem.,2018,42, e 12597). Furan is also an important organic synthetic reaction block and a basic skeleton constructed by high molecular materials ((a) ACS catalyst, 2021,11,10058-10083; b) Sustainable chem. Ser, 2018,2,217-237).
Selenium is an essential trace element in the human body. Researches show that the proper amount of selenium supplement can play roles in preventing organ aging and lesions, delaying aging, enhancing immunity, resisting diseases, resisting toxic heavy metals, relieving side effects of radiotherapy and chemotherapy and preventing and resisting cancers (chem. Rev.2004,104, 6255-6286). In addition, selenium-containing compounds have wide application in the fields of organic synthesis, pharmaceutical chemistry and material science. (Eur.J.org.chem., 2009, 1649-1664).
In view of the unique biological activity and physicochemical properties of furan skeletons and selenyls, development of novel efficient synthetic strategies to construct selenofurans has been the goal pursued by synthetic chemists. Conventional synthetic methods typically use an excess metal and an oxidizing agent in the presence of a suitable selenizing reagent to selenize the pre-prepared furan ring to give the target compound ((a) Asian J.org.chem.,2021,10,2975-2981), (b) Adv.Synth.catalyst, 2021,363,3577-3584, (c) chemistry select,2017,2,9227-9232, (d) Asian J.org.chem.,2015,4,875-878). In addition, the cyclization-selenization-based tandem reaction strategy is also an effective means of constructing selenofurans. Because the method can construct furan skeleton and form C-Se bond at the same time. For example, gilson Zeni et al disclose a phenyl selenium bromide-induced cyclization/selenization reaction of 2-alkynylanisole compounds to synthesize 3-selenylbenzofuran compounds (j.org.chem., 2009,74,2153-2162.). Benhur Godoi et al describe the CuI-catalyzed cyclization/selenization of 2-alkynylphenols in the presence of diselenylether to give 3-selenylbenzofurans (Eur. J. Org. Chem.,2017,2017,6382-6389). Luling Wu et al disclose a conjugated addition/cyclization/selenization domino reaction to synthesize 3-selenofuran compounds (org. Biomol. Chem.,2012,10,3705-3714.). Recently, suman De Sarkar et al disclosed an electrochemical method for the synthesis of 3-selenofuran from homopropynyl alcohol (J.org.chem., 2021,86,16084-16094).
As described above, various methods for preparing 3-selenofuran are disclosed in the prior art, but these methods have drawbacks such as the need for expensive transition metal and electrochemical reaction equipment, the use of chemical oxidants and air-sensitive selenizing reagents (ArSeX), and the severity of the reaction conditions.
Visible light is a clean and pollution-free energy source, and in recent years, visible light-promoted organic synthesis reactions have been greatly developed (m. -y.cao, x.ren and z.lu, tetrahedron lett.,2015,56,3732). However, literature studies indicate that the synthesis of 3-selenofuran based on tandem/selenization of high propargyl alcohol and diselenide ether with visible light participation has not been reported until now. For the reasons, it is still of great significance to explore a novel method for synthesizing 3-selenofuran compounds, which is efficient, environment-friendly, mild in reaction conditions, good in functional group compatibility and low in cost. This is the basis and motive force by which this application has been completed.
Disclosure of Invention
The invention aims to provide a method for synthesizing a 3-selenofuran compound by using visible light to solve the problems in the background technology.
In order to achieve the above purpose, the present invention provides the following technical solutions: a method for synthesizing a 3-selenofurans compound promoted by visible light comprises the following steps:
in an organic solvent, taking a high propargyl alcohol derivative with a structure shown in a formula (I), taking diselenide with a structure shown in a formula (II) as a reaction raw material, carrying out a reaction under the conditions of opening and room temperature and irradiation of visible light, decompressing reaction liquid after the reaction is finished, removing the solvent to obtain a crude product, and purifying the crude product through column chromatography to obtain the 3-selenofurans compound with the structure shown in the formula (III), wherein the reaction equation is shown as follows:
wherein the compound of formula (I) is a homopropargyl alcohol derivative, R1 and R2 are each independently selected from a hydrogen atom, a C1-C10 linear or branched alkyl group, a C1-C6 alkoxy group, a halogen, a cyano group, a nitro group, a trifluoromethyl group, a trifluoromethoxy group, and a formyl group.
The compound of formula (II) is diaryl diselenide or dialkyl diselenide, R3 can be selected from C1-C10 straight-chain or branched alkyl, benzyl, phenyl substituted by one or more substituents selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl and hydroxyl.
Preferably, the molar ratio of the 2-alkynylaniline of the structure of formula (I) to the diselenide of the structure of formula (II) is from 1:0.5 to 1:1, preferably 1:0.5.
Preferably, the organic solvent is at least one of dimethyl sulfoxide, N-dimethylformamide, ethyl acetate, N-hexane, tetrahydrofuran, 1, 4-dioxane, chloroform, 1, 2-dichloroethane, carbon tetrachloride and toluene, preferably N, N-Dimethylformamide (DMF).
Preferably, the visible light is any one of a fluorescent lamp, a tungsten lamp and an LED lamp.
Preferably, the reaction time is 30h-50h.
Preferably, after the reaction is finished, the reaction solution is concentrated under reduced pressure, the concentrate is separated by column chromatography, and the mixed solution of petroleum ether and ethyl acetate is used as an eluent, wherein the petroleum ether is as follows: the volume ratio of the ethyl acetate is (30-300): and 1, collecting eluent, and performing rotary evaporation on the solvent to obtain the 3-selenofuran shown in the formula (III).
Compared with the prior art, the invention has at least the following advantages:
(1) The invention can be carried out under the air condition, and has simple operation.
(2) The invention uses visible light as energy source and oxygen in air as oxidant, which meets the green chemical requirement.
(3) The invention does not use transition metal catalyst and chemical oxidant, and has high reaction selectivity, easy separation and purification of products and high yield.
(4) The invention only needs 0.5 equivalent of diselenide, and has good atom economy.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides the following technical scheme: a method for synthesizing a 3-selenofurans compound promoted by visible light comprises the following steps:
in an organic solvent, taking 2-alkynyl aniline with a structure shown in a formula (I) and diselenide with a structure shown in a formula (II) as reaction raw materials, carrying out reaction under the conditions of opening and room temperature and irradiation of visible light, decompressing reaction liquid after the reaction is finished, removing the solvent to obtain a crude product, and purifying the crude product through column chromatography to obtain the 3-selenofurans compound with the structure shown in the formula (III), wherein the reaction equation is shown as follows:
wherein the compound of formula (I) is a homopropargyl alcohol derivative, R1 and R2 are each independently selected from a hydrogen atom, a C1-C10 linear or branched alkyl group, a C1-C6 alkoxy group, a halogen, a cyano group, a nitro group, a trifluoromethyl group, a trifluoromethoxy group, and a formyl group.
The compound of formula (II) is diaryl diselenide or dialkyl diselenide, R3 can be selected from C1-C10 straight-chain or branched alkyl, benzyl, phenyl substituted by one or more substituents selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl and hydroxyl.
Example 1
The reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 1, 4-diphenyl-3-butyn-1-ol (0.2 mmol), diphenyl diselenide ether (0.1 mmol), DMF (1 ml) and a 23 w white compact fluorescent lamp were placed 1 cm from the reaction tube under open conditions, the reaction was carried out for 40 hours at room temperature, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (silica gel size: 200 to 300 mesh, eluent petroleum ether/ethyl acetate=100/1) to give 64 mg of the objective compound in 85% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ8.15(d,J＝7.9Hz,2H),7.78(d,J＝7.9Hz,2H),7.51(dd,J＝14.1,6.8Hz,6H),7.42-7.23(m,5H),6.81(s,1H). 13 C NMR(100MHz,CDCl 3 ):δ153.5,153.3,131.9,130.6,130.4,129.9,129.1,128.8,128.7,128.2,126.5,126.4,124.1,114.5,106.1.
example 2
The reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 1-phenyl-4- (4' -methylphenyl) -3-butyn-1-ol (0.2 mmol), diphenyl diselenide (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was freed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size: 200 to 300 mesh, eluent: petroleum ether/ethyl acetate=90/1) to give 65 mg of the objective compound in 83% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ7.90(d,J＝7.9Hz,2H),7.68(d,J＝7.9Hz,2H),7.38(t,J＝7.6Hz,4H),7.27(t,J＝7.4Hz,1H),7.30-7.19(m,5H),6.71(s,1H),2.39(s,3H). 13 C NMR(100MHz,CDCl 3 ):δ153.3,152.6,137.8,131.6,129.6,129.0,128.8,128.3,127.4,127.3,126.2,125.9,123.8,113.7,104.6,21.1.
example 3
The reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 1-phenyl-4- (4' -methoxyphenyl) -3-butyn-1-ol (0.2 mmol), diphenyl diselenide (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was freed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size: 200 to 300 mesh, eluent: petroleum ether/ethyl acetate=70/1) to give 65 mg of the objective compound in 80% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ8.01(d,J＝8.7Hz,2H),7.82-7.60(m,2H),7.50-7.26(m,4H),6.99(d,J＝8.8Hz,2H),6.79(s,1H),3.88(s,3H). 13 C NMR(100MHz,CDCl 3 ):δ159.2,153.9,152.5,132.0,130.1,129.5,129.1,128.8,127.9,127.3,126.0,123.5,123.1,113.9,113.8,103.5,55.1.
example 4
The reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 1-phenyl-4- (4' -chlorophenyl) -3-butyn-1-ol (0.2 mmol), diphenyl diselenide (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was freed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size 200 to 300 mesh, eluent petroleum ether/ethyl acetate=100/1) to give 73 mg of the objective compound in 89% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ7.88(d,J＝8.3Hz,2H),7.55(d,J＝8.0Hz,2H),7.33-7.24(m,5H),7.22-7.08(m,5H),6.62(s,1H). 13 C NMR(100MHz,CDCl 3 ):δ153.9,152.6,134.2,132.1,131.9,130.6,130.3,130.1,129.3,129.0,128.4,127.5,127.3,124.9,114.8,107.1.
example 5
The reaction equation is shown as follows:
10 ml of a reaction tube equipped with a magnetic stirrer was charged with 1-phenyl-4- (4' -methylphenyl) -3-butyn-1-ol (0.2 mmol), diphenyl diselenide (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was freed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size 200 to 300 mesh, eluent petroleum ether/ethyl acetate=60/1) to give 78 mg of the objective compound in 90% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ8.14-8.00(m,4H),7.79-7.72(m,2H),7.50-7.26(m,8H),6.75(s,1H),3.93(s,3H). 13 C NMR(100MHz,CDCl 3 ):δ166.0,153.1,151.0,133.9,130.1,128.8,128.7,128.6,128.0,127.4,126.5,124.9,124.8,123.5,113.3,108.3,51.6.
example 6
The reaction equation is shown as follows:
a10 ml reaction tube equipped with a magnetic stirrer was charged with 1-phenyl-4- (4' -cyanophenyl) -3-butyn-1-ol (0.2 mmol), diphenyl diselenide (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was freed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size 200 to 300 mesh, eluent petroleum ether/ethyl acetate=70/1) to give 72 mg of the objective compound in 90% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ8.18(d,J＝8.2Hz,2H),7.69(dd,J＝13.0,8.2Hz,4H),7.40(t,J＝7.7Hz,4H),7.36(t,J＝7.6Hz,1H),7.35(d,J＝5.2Hz,3H),6.69(s,1H). 13 C NMR(100MHz,CDCl 3 ):δ155.5,151.3,135.9,133.3,132.8,131.9,130.7,130.4,130.0,129.8,128.8,127.3,125.4,120.0,115.6,111.7,111.4.
example 7
The reaction equation is shown as follows:
10 ml of a reaction tube equipped with a magnetic stirrer was charged with 1- (4' -chlorophenyl) -4-phenyl-3-butyn-1-ol (0.2 mmol), diphenyl diselenide (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was freed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size 200 to 300 mesh, eluent petroleum ether/ethyl acetate=90/1) to give 71 mg of the objective compound in 87% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ8.06(d,J＝7.9Hz,2H),7.65(d,J＝8.5Hz,2H),7.45(dd,J＝9.9,5.4Hz,4H),7.39(d,J＝8.5Hz,2H),7.36-7.22(m,4H),6.75(s,1H). 13 C NMR(100MHz,CDCl 3 ):δ154.5,152.9,134.5,132.6,132.0,131.3,130.3,130.0,129.5,129.1,129.0,128.2,127.5,126.1,115.1,107.1.
example 8
The reaction equation is shown as follows:
10 ml of a reaction tube equipped with a magnetic stirrer was charged with 1- (4' -bromophenyl) -4-phenyl-3-butyn-1-ol (0.2 mmol), diphenyl diselenide (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was freed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size 200 to 300 mesh, eluent petroleum ether/ethyl acetate=90/1) to give 74 mg of the objective compound in 82% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ8.00(d,J＝7.9Hz,2H),7.53(d,J＝8.2Hz,2H),7.49(d,J＝8.4Hz,2H),7.40-7.17(m,8H),6.69(s,1H). 13 C NMR(100MHz,CDCl 3 ):δ153.0,151.7,131.9,131.73,130.1,129.1,128.2,128.1,128.0,127.3,126.6,125.9,125.0,121.7,113.8,105.8.
example 9
The reaction equation is shown as follows:
10 ml of a reaction tube equipped with a magnetic stirrer was charged with 1, 4-diphenyl-3-butyn-1-ol (0.2 mmol), bis (4-methylphenyl) diselenide ether (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (silica gel size 200 to 300 mesh, eluent petroleum ether/ethyl acetate=90/1) to give 68 mg of the objective compound in 88% yield.
The nuclear magnetic spectrum data of the obtained product are: 7.87-7.60 (m, 5H), 7.51-7.40 (m, 4H), 7.28 (d J =7.9 hz, 2H), 7.21-7.16 (m, 3H), 6.69 (s, 1), 2.32 (s, 3H). 13 C NMR(100MHz,CDCl 3 ):δ152.1,149.6,135.7,136.2,133.8,133.0,132.9,130.7,130.1,129.0,128.9,128.8,127.3,125.1,114.7,106.3,21.6.
Example 10
The reaction equation is shown as follows:
10 ml of a reaction tube equipped with a magnetic stirrer was charged with 1, 4-diphenyl-3-butyn-1-ol (0.2 mmol), bis (4-methoxyphenyl) diselenide ether (0.1 mmol), DMF (1 ml) was added, a 23 w white compact fluorescent lamp was placed at a distance of 1 cm from the reaction tube, the reaction was carried out at room temperature for 40 hours under open conditions, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (silica gel size: 200 to 300 mesh, eluent: petroleum ether/ethyl acetate=90/1) to give 66 mg of the objective compound in 82% yield.
The nuclear magnetic spectrum data of the obtained product are: 1 H NMR(400MHz,CDCl 3 ):δ8.09(d,J＝8.0Hz,2H),7.74(d,J＝7.9Hz,2H),7.52-7.40(m,6H),7.39-7.25(m,2H),6.88(d,J＝8.6Hz,2H),6.65(s,1H),3.82(s,3H). 13 C NMR(100MHz,CDCl 3 ):δ150.1,153.5,152.3,134.6,131.3,130.9,129.3,128.9,128.5,126.6,124.7,121.6,115.8,113.6,108.7,56.1.
in summary, the preparation method of the invention takes the high propargyl alcohol and diselenide as raw materials, and takes at least one of dimethyl sulfoxide, N-dimethylformamide, ethyl acetate, N-hexane, tetrahydrofuran, 1, 4-dioxane, chloroform, 1, 2-dichloroethane, carbon tetrachloride and toluene, the reaction temperature is room temperature, and the white fluorescent lamp is irradiated under the open condition to efficiently synthesize the 3-selenofuran compound, and compared with the traditional synthesis method, the method has mild reaction condition and can be smoothly carried out at room temperature; the operation is simple, and all operations can be performed in an open system; meanwhile, the method avoids the use of expensive transition metal catalysts, photocatalysts and oxidants, and has the characteristics of economy, environment friendliness and the like.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (5)

1. A method for synthesizing a 3-selenofurans compound promoted by visible light is characterized by comprising the following steps: the method comprises the following steps: in an organic solvent, taking a high propargyl alcohol derivative with a structure shown in a formula (I), taking diselenide with a structure shown in a formula (II) as a reaction raw material, carrying out a reaction under the conditions of opening and room temperature and irradiation of visible light, decompressing reaction liquid after the reaction is finished, removing the solvent to obtain a crude product, and purifying the crude product through column chromatography to obtain the 3-selenofurans compound with the structure shown in the formula (III), wherein the reaction equation is shown as follows:
wherein the compound of formula (I) is a homopropargyl alcohol derivative, R1 and R2 are each independently selected from a hydrogen atom, a C1-C10 linear or branched alkyl group, a C1-C6 alkoxy group, a halogen, a cyano group, a nitro group, a trifluoromethyl group, a trifluoromethoxy group, a formyl group;
the compound of the formula (II) is diaryl diselenide or dialkyl diselenide, R3 is selected from C1-C10 straight-chain or branched-chain alkyl, benzyl and phenyl substituted by one or more substituents, wherein the substituents are selected from C1-C10 alkyl, C1-C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl and hydroxyl;
the organic solvent is N, N-dimethylformamide; the visible light is a fluorescent lamp.
2. The method for synthesizing the 3-selenofuran compound promoted by visible light according to claim 1, wherein the method comprises the following steps: the molar ratio of the 2-alkynyl aniline with the structure shown in the formula (I) to the diselenide with the structure shown in the formula (II) is 1:0.5-1:1.
3. The method for synthesizing the 3-selenofuran compound promoted by visible light according to claim 2, wherein the method comprises the following steps: the molar ratio of the 2-alkynyl aniline of the structure shown in the formula (I) to the diselenide of the structure shown in the formula (II) is 1:0.5.
4. The method for synthesizing the 3-selenofuran compound promoted by visible light according to claim 1, wherein the method comprises the following steps: the reaction time is 30-50 h.
5. The method for synthesizing the 3-selenofuran compound promoted by visible light according to claim 1, wherein the method comprises the following steps: after the reaction is finished, the reaction solution is decompressed and concentrated, the concentrate is separated by column chromatography, and the mixed solution of petroleum ether and ethyl acetate is used as eluent, wherein the petroleum ether is as follows: the volume ratio of the ethyl acetate is (30-300): and 1, collecting eluent, and performing rotary evaporation on the solvent to obtain the 3-selenofuran shown in the formula (III).
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