CN110627840B - Method for preparing 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methinone - Google Patents
Method for preparing 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methinone Download PDFInfo
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Abstract
The invention discloses a method for preparing 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methine acetone, which comprises the following steps: adding choline chloride and urea into a dry three-neck flask, and stirring at 80 ℃ until a transparent solution is obtained to obtain a eutectic solvent (DES); cooling to room temperature, adding ferrocenyl chalcone and ethyl acetoacetate, slowly heating, performing reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is finished to obtain 1-ferrocenyl-3-aryl- (1-acetyl-1-ethoxycarbonyl) methicone, wherein the yield can reach over 86%; the eutectic solvent (DES) obtained by concentrating and recovering the filtrate can be reused, and the catalytic activity of the DES is not obviously reduced. The invention provides a method which is green, environment-friendly, efficient, simple to operate and low in toxicity for the synthesis of the compounds, and simultaneously the catalyst can be recycled, so that the reaction cost is reduced.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for preparing 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methinone.
Background
Michael addition is one of important reactions for constructing carbon-carbon bonds in organic synthesis, the formation of the carbon-carbon bonds is very important for the synthesis of complex organic molecules, and some active methylene compounds such as ethyl cyanoacetate, malononitrile, nitromethane and alpha, beta unsaturated ketone are added, so that the synthesis of hydrogenated pyridine derivatives, ketonitriles and ketone nitro derivatives with important functions is facilitated.
Most of the existing methods for preparing ferrocenyl chalcone are solvent method and solid phase grinding method. The grinding method is to activate the system by increasing the total free energy of the reaction system through the heat generated by external force friction, so as to accelerate the reaction process, but the dosage of the strong base used as the catalyst in the grinding method is large, the strong base cannot be recycled, and the cost is higher. In general, the common solvent method utilizes strong base as a catalyst, the reaction time is long, the toxicity of an organic solvent is high, and a plurality of side reactions are also caused by the violent action of the strong base.
Disclosure of Invention
The invention aims to provide a method for preparing a compound 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methine acetone, which does not need an organic solvent, is green and environment-friendly, has high yield, simple operation and low toxicity, and can recycle a catalyst for 5 times.
In order to achieve the purpose, the invention adopts the following technical scheme:
a process for 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methione comprising the steps of:
step one, adding A mol of choline chloride and B mol of urea into a reaction vessel, and stirring at 80 ℃ until a transparent solution is obtained to obtain a eutectic solvent;
step two, cooling the reaction system to room temperature, adding C mol of ferrocenyl chalcone and D mol of ethyl acetoacetate, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished (20-40 min);
and thirdly, cooling the reaction solution to room temperature, adding a small amount of water, immediately separating out solids, performing suction filtration, washing a filter cake with a small amount of water, and performing vacuum drying to obtain the 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methine acetone, and recovering the filtrate to obtain a eutectic solvent which can be recycled for 5 times.
The structural formula of the choline chloride is as follows:
the structural formula of the urea is as follows:
in the step, the molar ratio of choline chloride to urea to ferrocenyl chalcone to ethyl acetoacetate is 1:2:0.01 (0.01-0.013).
The choline chloride and the urea are stirred at the temperature of 80 ℃ until being completely dissolved to obtain the eutectic solvent which is used as both the solvent and the catalyst.
The aryl in the ferrocenyl chalcone is phenyl, halogenated phenyl, methylphenyl, ethylphenyl, propylphenyl, methoxyphenyl, nitrophenyl, hydroxyphenyl, aminophenyl, styryl, five-membered heterocyclic group or six-membered heterocyclic group;
the halogenated phenyl is o-fluorophenyl, p-fluorophenyl, o-chlorophenyl, p-chlorophenyl, 2, 4-dichlorophenyl, o-bromophenyl, m-bromophenyl or p-bromophenyl;
the methyl phenyl is o-methyl phenyl, m-methyl phenyl or p-methyl phenyl;
the ethyl phenyl is m-ethyl phenyl and p-ethyl phenyl;
the propyl phenyl is n-propyl phenyl and isopropyl phenyl;
the methoxyphenyl is m-methoxyphenyl or p-methoxyphenyl;
the nitrophenyl is m-nitrophenyl, 3, 5-dinitrophenyl or p-nitrophenyl;
the five-membered heterocyclic group is furyl or thienyl;
the six-membered heterocyclic group is pyridyl.
The reaction mechanism of the invention is as follows: the eutectic solvent is obtained by stirring choline chloride and urea at 80 ℃ until the choline chloride and the urea are completely dissolved, and is used for catalyzing the ferrocenyl chalcone and the ethyl acetoacetate to carry out Michael addition to prepare the 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methicone.
The structural formula of the 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methylidyneacetone is shown in the specification;
compared with the prior art, the invention has the following advantages:
firstly, the method comprises the following steps: the method of the invention has simple operation and high yield;
secondly, the method comprises the following steps: the catalyst can be recycled, and the cost is reduced;
thirdly, the method comprises the following steps: the catalyst is used, organic solvent is not needed, and the catalyst is more green and environment-friendly;
fourthly: overcomes the defects of large consumption and non-recoverability of the alkaline catalyst in the grinding method.
Drawings
FIG. 1 shows 1-ferrocenyl-3-phenyl-3- (1-acetyl-1-ethoxycarbonyl) methinone1HNMR spectrogram;
FIG. 2 shows 1-ferrocenyl-3-phenyl-3- (1-acetyl-1-ethoxycarbonyl) methinone13CNMR spectrogram;
FIG. 3 shows 1-ferrocenyl-3-p-chlorophenyl-3- (1-acetyl-1-ethoxycarbonyl) methylidyneacetone1HNMR spectrogram;
FIG. 4 shows 1-ferrocenyl-3-p-chlorophenyl-3- (1-acetyl-1-ethoxycarbonyl) methinone13CNMR spectrogram;
FIG. 5 shows 1-ferrocenyl-3-p-methylphenyl-3- (1-acetyl-1-ethoxycarbonyl) methinone1HNMR spectrogram;
FIG. 6 shows 1-ferrocenyl-3-p-methylphenyl-3- (1-acetyl-1-ethoxycarbonyl) methinone13CNMR spectrogram.
Detailed Description
The invention relates to a method for preparing 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methine, which comprises the following steps of firstly obtaining eutectic solvent by choline chloride and urea, then adding ferrocenyl chalcone and ethyl acetoacetate into a reactor to react to prepare 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methine, wherein the reaction formula is as follows:
wherein aryl substituents are phenyl, p-chlorophenyl, p-bromophenyl, p-fluorophenyl, p-methylphenyl, p-ethylphenyl, m-ethylphenyl, n-propylphenyl, isopropylphenyl, p-methoxyphenyl, m-nitrophenyl, p-hydroxyphenyl, o-hydroxyphenyl, vinylphenyl, o-methylphenyl, m-methoxyphenyl, 2-fluorophenyl, p-aminophenyl, m-aminophenyl, o-chlorophenyl, 2, 4-dichlorophenyl, p-nitrophenyl, 3, 5-dinitrophenyl, o-bromophenyl, m-bromophenyl, furyl, thienyl, pyridyl and the like.
The present invention will be described in further detail with reference to specific examples thereof, but the present invention is not limited thereto.
Example 11-preparation of ferrocenyl-3-phenyl-3- (1-acetyl-1-ethoxycarbonyl) methione:
step one, adding 1mol of choline chloride and 2mol of urea into a reaction container, and stirring at 80 ℃ until the choline chloride and the urea are completely dissolved to obtain a eutectic solvent;
secondly, cooling the reaction system to room temperature, adding 1-ferrocenyl-3-aryl-acrylketone 0.01mol and ethyl acetoacetate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished;
and thirdly, cooling the reaction liquid to room temperature, separating out a solid, performing suction filtration, and washing a filter cake with a small amount of water to obtain the 1-ferrocenyl-3-phenyl-3- (1-acetyl-1-ethoxycarbonyl) methylidyneacetone. The yield is 87.4%, and m.p. is 129-130 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 87.1%, the 2 nd yield of the eutectic solvent was 86.8%, the 3 rd yield of the eutectic solvent was 86.2%, the 4 th yield of the eutectic solvent was 85.7%, and the 5 th yield of the eutectic solvent was 85%.
The structural characterization data for the product is:
IR(KBr)ν:2985,2865,1423(-CH2),1719,1647(C＝O),1594, 1451(Ar-H)；
1HNMR(400Hz,DMSO-d6)δ:7.68-7.70(d,2H,Ph-H),7.45-7.46(d, 2H,Ph-H),7.29(d,1H,Ph-H),4.93(s,2H,Fe-H),4.50(s,2H,Fe-H), 4.25(s,5H,Fe-H),4.08-4.10(q,2H,-COOCH2),3.61-3.76(m,2H,-CH), 2.69-2.70(d,2H,-OCH2),2.19(s,3H,-COCH3),1.19-1.22(t,3H, -CH2CH3)；
13CNMR(100MHz,DMSO-d6)δ:201.68,192.98,169.48,149.08, 136.25,122.43,119.55,71.85,69.70,68.99,60.27,57.84,44.96,33.74, 27.45,13.78.
example 21 preparation of ferrocenyl-3- (p-fluorophenyl) -3- (1-acetyl-1-ethoxycarbonyl) methinone:
step one, adding 1mol of choline chloride and 2mol of urea into a reaction container, and stirring at 80 ℃ until the choline chloride and the urea are completely dissolved to obtain a eutectic solvent;
secondly, cooling the reaction system to room temperature, adding 1-ferrocenyl-3- (p-fluorophenyl) -acrylketone 0.01mol and ethyl acetoacetate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished;
and thirdly, cooling the reaction liquid to room temperature, separating out a solid, performing suction filtration, and washing a filter cake with a small amount of water to obtain the 1-ferrocenyl-3- (p-fluorophenyl) -3- (1-acetyl-1-ethoxycarbonyl) methylidyneacetone. The yield is 86.5%, and the m.p. is 137-139 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 86.3%, the 2 nd yield of the eutectic solvent was 86%, the 3 rd yield of the eutectic solvent was 85.4%, the 4 th yield of the eutectic solvent was 84.6%, and the 5 th yield of the eutectic solvent was 84.1%.
The structural characterization data for the product is:
IR(KBr)ν:2994,2875,1712,1649(C＝O),1592,1485,1453(Ar-H), 1438(-CH2),1372(-CH3)；
1HNMR(400MHz,DMSO-d6)δ:7.60-7.66(d，2H，Ph-H),7.40-7.45(d, 2H,Ph-H),4.90(s,2H,Fe-H),4.62(s,2H,Fe-H),4.25(s,5H，Fe-H), 4.08-4.12(q,2H,-COOCH2),3.60-3.74(m,2H,-CH),2.68-2.71(d,2H, -OCH2),2.17(s,3H,-COCH3),1.18-1.21(t,3H,-CH2CH3)；
13CNMR(100MHz,DMSO-d6):200.60,192.17,170.70,140.01, 132.83,129.13,123.00,80.01,72.40,69.68,43.64,26.00,23.74,19.65.
example 31 preparation of ferrocenyl-3- (p-chlorophenyl) -3- (1-acetyl-1-ethoxycarbonyl) methinone:
step one, adding 1mol of choline chloride and 2mol of urea into a reaction container, and stirring at 80 ℃ until the choline chloride and the urea are completely dissolved to obtain a eutectic solvent;
secondly, cooling the reaction system to room temperature, adding 1-ferrocenyl-3- (p-chlorophenyl) -acrylketone 0.01mol and ethyl acetoacetate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is finished;
and thirdly, cooling the reaction liquid to room temperature, separating out a solid, performing suction filtration, and washing a filter cake with a small amount of water to obtain the 1-ferrocenyl-3- (p-chlorophenyl) -3- (1-acetyl-1-ethoxycarbonyl) methicone. The yield is 87.2%, and m.p. is 143-144 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 87.1%, the 2 nd yield of the eutectic solvent was 86.6%, the 3 rd yield of the eutectic solvent was 86.1%, the 4 th yield of the eutectic solvent was 85.5%, and the 5 th yield of the eutectic solvent was 85.1%.
The structural characterization data for the product is:
IR(KBr)ν:2993,2870,1721,1649(C＝O),1591,1494,1453(Ar-H), 1425(-CH2),1378(-CH3)；
1HNMR(400MHz,DMSO-d6)δ:7.61-7.68(d,2H,Ph-H),7.41-7.43(d, 2H,Ph-H),4.90(s,2H,Fe-H),4.62(s,2H,Fe-H),4.25(s,5H,Fe-H), 4.08-4.12(q,2H,-COOCH2),3.61-3.76(m,2H,-CH),2.69-2.70(d, 2H,-OCH2),2.19(s,3H,-COCH3),1.19-1.22(t,3H,-CH2CH3)；
13CNMR(100MHz,DMSO-d6):200.62,192.20,170.74,138.98, 132.80,129.15,122.99,79.98,72.44,69.65,43.60,26.00,23.71,19.67.
example 41-preparation of ferrocenyl-3- (p-bromophenyl) -3- (1-acetyl-1-ethoxycarbonyl) methinone:
step one, adding 1mol of choline chloride and 2mol of urea into a reaction container, and stirring at 80 ℃ until the choline chloride and the urea are completely dissolved to obtain a eutectic solvent;
secondly, cooling the reaction system to room temperature, adding 1-ferrocenyl-3- (p-bromophenyl) -acrylketone 0.01mol and ethyl acetoacetate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is finished;
and thirdly, cooling the reaction liquid to room temperature, separating out a solid, performing suction filtration, and washing a filter cake with a small amount of water to obtain the 1-ferrocenyl-3- (p-bromophenyl) -3- (1-acetyl-1-ethoxycarbonyl) methicone. The yield is 87.2%, and the m.p. is 162-163 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 87% after repeated use, 86.6% after repeated use, 86.2% after repeated use, 85.5% after repeated use, and 85% after repeated use, 5% after repeated use.
The structural characterization data for the product is:
IR(KBr)ν:2987,2877,1712,1649(C＝O),1592,1485,1453(Ar-H), 1415(-CH2),1375(-CH3)；
1HNMR(400MHz,DMSO-d6)δ:7.63-7.70(d,2H,Ph-H),7.40-7.45(d, 2H,Ph-H),4.89(s,2H,Fe-H),4.52(s,2H,Fe-H),4.24(s,5H,Fe-H), 4.05-4.09(q,2H,-COOCH2),3.62-3.74(m,2H,-CH),2.71-2.73(d, 2H,-OCH2),2.20(s,3H,-COCH3),1.17-1.21(t,3H,-CH2CH3)；
13CNMR(100MHz,DMSO-d6):200.35,192.40,170.70,139.00, 132.85,129.30,123.03,80.01,72.45,69.67,43.70,26.01,23.75,18.97.
example 51-preparation of ferrocenyl-3- (p-methylphenyl) -3- (1-acetyl-1-ethoxycarbonyl) methinone:
step one, adding 1mol of choline chloride and 2mol of urea into a reaction container, and stirring at 80 ℃ until the choline chloride and the urea are completely dissolved to obtain a eutectic solvent;
secondly, cooling the reaction system to room temperature, adding 1-ferrocenyl-3- (p-methylphenyl) -acrylketone 0.01mol and ethyl acetoacetate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is finished;
and thirdly, cooling the reaction liquid to room temperature, separating out a solid, performing suction filtration, and washing a filter cake with a small amount of water to obtain the 1-ferrocenyl-3- (p-methylphenyl) -3- (1-acetyl-1-ethoxycarbonyl) methicone. The yield is 86.4%, and m.p. is 157-158 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 86.2%, the 2 nd yield of the eutectic solvent was 85.7%, the 3 rd yield of the eutectic solvent was 85.2%, the 4 th yield of the eutectic solvent was 84.5%, and the 5 th yield of the eutectic solvent was 84.1%.
The structural characterization data for the product is:
IR(KBr)ν:2989,1376(-CH3),2897,1412(-CH2),1717,1646(C＝O), 1586,1513,1451(Ar-H)；
1HNMR(400MHz,DMSO-d6)δ:7.78-7.80(d,2H,Ph-H),7.60-7.62(d, 2H,Ph-H),4.82(s,2H,Fe-H),4.44(s,2H,Fe-H),4.31(s,5H,Fe-H), 3.95-4.29(q,2H,-COOCH2),3.81-3.84(m,2H,-CH),2.88-2.89(d,2H, -OCH2),2.37(s,3H,-COCH3),2.09(s,3H,-CH3),1.19-1.22(t,3H, -CH2CH3)；
13CNMR(100MHz,DMSO-d6):200.62,192.20,170.74,138.98, 131.72,129.15,123.00,80.05,72.45,69.57,43.6,26.02,23.72,22.00, 19.65。
Claims (7)
1. a method for preparing 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methinone, which is characterized by comprising the following steps:
catalyzing Michael addition reaction of ferrocenyl chalcone and ethyl acetoacetate by using a choline chloride/urea eutectic solvent; after the reaction is finished, cooling the reaction liquid to room temperature, adding a small amount of water, immediately separating out solids, performing suction filtration to obtain a filter cake, washing the filter cake with water, and performing vacuum drying to obtain 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methine acetone; and recovering the filtrate to obtain the eutectic solvent.
2. The method as claimed in claim 1, wherein choline chloride and urea are dissolved by heating in a molar ratio of 1:2 to obtain a choline chloride/urea eutectic solvent.
3. The method according to claim 1, wherein the molar ratio of ferrocenyl chalcone to ethyl acetoacetate is 1 (1.0-1.3).
4. The method of claim 1, wherein the choline chloride has the formula:
5. the method of claim 1, wherein the ferrocenyl chalcone has a formula:
ar is phenyl, halogenated phenyl, methylphenyl, ethylphenyl, propylphenyl, methoxyphenyl, nitrophenyl, hydroxyphenyl, aminophenyl, styryl, a five-membered heterocyclic group or a six-membered heterocyclic group.
6. The method of claim 5, wherein the halophenyl group is an o-fluorophenyl group, a p-fluorophenyl group, an o-chlorophenyl group, a p-chlorophenyl group, a 2, 4-dichlorophenyl group, an o-bromophenyl group, a m-bromophenyl group, or a p-bromophenyl group; the methyl phenyl is o-methyl phenyl, m-methyl phenyl or p-methyl phenyl; the methoxyphenyl is m-methoxyphenyl or p-methoxyphenyl; the ethyl phenyl is m-ethyl phenyl and p-ethyl phenyl; the propyl phenyl is n-propyl phenyl and isopropyl phenyl; the nitrophenyl is m-nitrophenyl, 3, 5-dinitrophenyl or p-nitrophenyl; the hydroxyphenyl is o-hydroxyphenyl or p-hydroxyphenyl; the aminophenyl is o-aminophenyl, m-aminophenyl or p-aminophenyl; the five-membered heterocyclic group is furyl or thienyl; the six-membered heterocyclic group is pyridyl.
7. The method of claim 2, wherein the specific steps comprise:
1) adding A mol of choline chloride and B mol of urea into a dry three-neck flask, and stirring at 80 ℃ until a transparent solution is obtained to obtain a eutectic solvent;
2) cooling the mixture to room temperature, adding C mol of ferrocenyl chalcone and D mol of ethyl acetoacetate, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is complete; wherein A, B, C, D, 1, 2, 0.01, (0.01-0.013).
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| CN103992356A (en) * | 2014-05-04 | 2014-08-20 | 陕西科技大学 | Michael addition product of ferrocene-based chalcone and ethyl acetoacetate and preparation method thereof |
Non-Patent Citations (3)
| Title |
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| Deep Eutectic Solvents in Organic Synthesis;Scott T. Handy;《Ionic Liquids - Current State of the Art》;20151231;第3卷;第59-92页 * |
| Synergistic effect of ultrasound and deep eutectic solvent choline chloride–urea as versatile catalyst for rapid synthesis of β-functionalized ketonic derivatives;Urmiladevi Narad Yadav等;《Journal of Molecular Liquids》;20140311;第195卷;第188-193页 * |
| 低共熔溶剂中新型螺环吲哚衍生物的绿色合成;严楠等;《有机化学》;20141121;第35卷;第384-389页 * |
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