CN110804076A - Method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methine) -acetone - Google Patents
Method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methine) -acetone Download PDFInfo
- Publication number
- CN110804076A CN110804076A CN201911155156.6A CN201911155156A CN110804076A CN 110804076 A CN110804076 A CN 110804076A CN 201911155156 A CN201911155156 A CN 201911155156A CN 110804076 A CN110804076 A CN 110804076A
- Authority
- CN
- China
- Prior art keywords
- group
- ferrocenyl
- aryl
- reaction
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate 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; cooling to room temperature, adding ferrocenyl chalcone and diethyl malonate, slowly heating, carrying out reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is finished; cooling the reaction mixture to room temperature, adding a small amount of water, immediately separating out solids, performing suction filtration, washing a filter cake with water, and drying to obtain the 1-ferrocenyl-3-aryl- (ethyl dicarboxylate group methine) -acetone with the yield of more than 81%; the filtrate is concentrated and recovered to obtain the eutectic solvent which can be repeatedly used. The invention provides a simple, green and environment-friendly method for synthesizing 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- (ethyl dicarboxylate group methine) -acetone.
Background
The ferrocenyl chalcone can generate Michael addition reaction with hydrazine, thiourea, nitrile, active methylene compound or amine and the like to generate heterocyclic compounds with ferrocenyl, and a method is provided for developing more ferrocenyl heterocyclic derivatives with bioactivity.
Most of the existing methods for preparing ferrocenyl chalcone are solvent method and solid phase grinding method. The grinding method is to increase the total free energy of the reaction system by external force friction heat generation to activate the system and accelerate the reaction process, but the grinding method uses alkali as a catalyst to obtain a product by suction filtration, and the catalyst cannot be recycled, so that the cost is high. The general solvent method utilizes strong base as a catalyst, and the violent action of the strong base often causes a plurality of side reactions, such as substrate self-condensation, rearrangement, double addition, further condensation or cracking of addition products, anti-Michael addition, polymerization and the like, so that the yield of the obtained product is low, and a plurality of inconveniences are brought to the purification of the product.
Disclosure of Invention
The invention aims to provide a method for preparing a compound 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate methine) -acetone, which is green, environment-friendly, high in yield, simple to operate and recyclable in catalyst.
In order to achieve the purpose, the invention adopts the following technical scheme:
a process for 1-ferrocenyl-3-aryl-3- (carbethoxymethine) -propanone comprising the steps of:
step one, adding A mol of choline chloride and B mol of urea into a reaction container, and stirring at 80 ℃ until a transparent solution is obtained to obtain a eutectic solvent;
secondly, cooling the reaction system to room temperature, adding 1-ferrocenyl-3-aryl-acrylketone and Dmol diethyl malonate in a C mol manner, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished (20-40 min);
and thirdly, cooling the reaction liquid 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, performing vacuum drying to obtain the 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methylene) -acetone, and recovering the filtrate to obtain the eutectic solvent.
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 diethyl malonate 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 1-ferrocenyl-3-aryl-acrylketone is phenyl, halogenated phenyl, methylphenyl, ethylphenyl, propylphenyl, methoxyphenyl, nitrophenyl, hydroxyphenyl, aminophenyl, 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 1-ferrocenyl-3-aryl-acrylketone and diethyl malonate to perform Michael addition to prepare 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate methine) -acetone.
The structural formula of the 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methine) -acetone 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 more green and environment-friendly;
fourthly: the defect that the alkaline catalyst cannot be recycled in a grinding method is overcome;
drawings
FIG. 1 is a drawing showing the preparation of 1-ferrocenyl-3-p-chlorophenyl-3- (ethylcarbamoylmethine) -propanone1HNMR spectrogram;
FIG. 2 is a drawing showing the preparation of 1-ferrocenyl-3-p-chlorophenyl-3- (ethylcarbamoylmethine) -propanone13CNMR spectrogram;
FIG. 3 is a drawing showing the preparation of 1-ferrocenyl-3-p-methylphenyl-3- (ethylcarbamoylmethine) -acetone1HNMR spectrogram;
FIG. 4 is a drawing showing the preparation of 1-ferrocenyl-3-p-methylphenyl-3- (ethylcarbamoylmethine) -acetone13CNMR spectrogram;
FIG. 5 is a drawing showing the preparation of 1-ferrocenyl-3-p-methoxyphenyl-3- (ethylcarbamoylmethine) -propanone1HNMR spectrogram;
FIG. 6 is a drawing showing the preparation of 1-ferrocenyl-3-p-methoxyphenyl-3- (ethylcarbamoylmethine) -propanone13CNMR spectrogram.
Detailed Description
The invention relates to a method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate methine) -acetone, which comprises the steps of firstly obtaining eutectic solvent from choline chloride and urea, then adding 1-ferrocenyl-3-aryl-acrylketone and diethyl malonate into a reactor to react to prepare 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate methine) -acetone, wherein the reaction formula is as follows:
wherein the aryl substituent is phenyl, p-chlorophenyl, p-bromophenyl, p-fluorophenyl, p-methylphenyl, p-ethylphenyl, m-ethylphenyl, n-propylphenyl, isopropylphenyl, p-methoxyphenyl, m-nitrophenyl, p-hydroxyphenyl, 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, etc.
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- (ethylcarbamoylmethine) -propanone:
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 diethyl malonate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished (25 min);
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- (ethyl dicarboxylate methine) -acetone. The yield is 83.4%, and m.p. is 110-112 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 83.1%, the 2 nd yield of the eutectic solvent was 82.8%, the 3 rd yield of the eutectic solvent was 82.3%, the 4 th yield of the eutectic solvent was 82%, and the 5 th yield of the eutectic solvent was 81.8%.
The structural characterization data for the product is:
IR(KBr)ν:2982,2875,1650,1600(C=O),1582,1452(Ar-H),1420(-CH2),1370(-CH3);
1HNMR(400MHz,DMSO-d6)δ:7.67-7.69(d,2H,Ph-H),7.45-7.46(d,2H,Ph-H),7.28(d,1H,Ph-H),4.94(s,2H,Fe-H),4.44(s,2H,Fe-H),4.25(s,5H,Fe-H),4.11-4.13(q,4H,-COOCH2),3.31-3.38(m,2H,-CH),2.69(d,2H,-OCH2),1.19-1.22(t,6H,-CH2CH3);
13CNMR(100MHz,DMSO-d6)δ:193.14,170.31,135.23,130.11,128.28,80.65,70.12,69.76,59.29,53.44,42.24,26.41,13.89.
example 21-preparation of ferrocenyl-3- (p-bromophenyl) -3- (ethylcarbamoylmethine) -acetone:
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 diethyl malonate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished (30 min);
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- (ethyl dicarboxylate methine) -acetone. The yield is 86.6%, and m.p. is 116-117 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 86.4% after repeated use, the 2 nd yield was 86%, the 3 rd yield was 85.7%, the 4 th yield was 85.3%, and the 5 th yield was 85%.
The structural characterization data for the product is:
IR(KBr)ν:2983,2889,1674,1630(C=O),1585,1450(Ar-H),1430(-CH2),1372(-CH3);
1HNMR(400MHz,DMSO-d6)δ:7.46-7.53(d,2H,Ph-H),7.32-7.38(d,2H,Ph-H),4.99(s,2H,Fe-H),4.59(s,2H,Fe-H),4.26(s,5H,Fe-H),4.12-4.16(q,4H,-COOCH2),3.42-3.78(m,2H,-CH),2.68-2.70(d,2H,-OCH2),1.20-1.24(t,6H,-CH2CH3);
13CNMR(100MHz,DMSO-d6):193.02,170.31,140.21,134.99,134.12,129.33,80.50,71.99,69.85,62.01,54.84,45.03,28.95,14.92.
example 31 preparation of ferrocenyl-3- (p-methoxyphenyl) -3- (ethylcarbamoylmethine) -propanone:
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-methoxyphenyl) -acrylketone 0.01mol and diethyl malonate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished (30 min);
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-methoxyphenyl) -3- (ethyl dicarboxylate methine) -acetone. The yield is 85.8%, and the m.p. is 135-136 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 85.4%, the 2 nd yield of the eutectic solvent was 85.2%, the 3 rd yield of the eutectic solvent was 84.7%, the 4 th yield of the eutectic solvent was 84.3%, and the 5 th yield of the eutectic solvent was 84.1%.
The structural characterization data for the product is:
IR(KBr)ν:2988,2889,1682,1643(C=O),1580,1458(Ar-H),1432(-CH2),1373(-CH3);
1HNMR(400MHz,DMSO-d6)δ:7.62-7.64(d,2H,Ph-H),6.97-6.99(d,2H,Ph-H),5.08(s,2H,Fe-H),4.61(s,2H,Fe-H),4.24(s,5H,Fe-H),4.08-4.10(q,4H,-COOCH2),3.90(s,3H,-OCH3),3.38-3.57(m,2H,-CH),2.69-2.70(d,2H,-OCH2),1.19-1.22(t,6H,-CH2CH3);
13CNMR(100MHz,DMSO-d6):193.01,161.35,140.66,129.96,120.80,114.42,80.05,72.58,69.69,58.01,55.43,52.37,44.73,25.37,16.39.
example 41-preparation of ferrocenyl-3- (isopropylphenyl) -3- (ethyldicarboxylate methine) -acetone:
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- (isopropylphenyl) -acrylketone 0.01mol and diethyl malonate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished (35 min);
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- (isopropylphenyl) -3- (ethyl dicarboxylate methine) -acetone. The yield is 87%, and m.p. is 116-117 ℃; and recovering the filtrate to obtain the eutectic solvent. The 1 st yield of the eutectic solvent was 86.8%, the 2 nd yield of the eutectic solvent was 86.5%, 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 85.4%.
The structural characterization data for the product is:
IR(KBr)ν:2989,2883,1685,1640(C=O),1587,1454(-CH2),1451(Ar-H),1374(-CH3);
1HNMR(400MHz,DMSO-d6)δ:7.60-7.62(d,2H,Ph-H),7.42-7.44(d,2H,Ph-H),5.10(s,2H,Fe-H),4.41(s,2H,Fe-H),4.29(s,5H,Fe-H),4.26-4.27(q,2H,-COOCH2),3.11-3.42(m,3H,-CH),2.69-2.70(d,2H,-OCH2),1.49-1.53(d,2H,-CH(CH3)2),1.19-1.22(t,3H,-CH2CH3);
13CNMR(100MHz,DMSO-d6):200.52,167.57,147.24,137.66,127.90,125.88,80.02,71.51,69.09,61.06,56.84,43.34,39.39,33.22,23.49,13.27.
example 51-preparation of ferrocenyl-3- (vinylphenyl) -3- (ethylcarbamoylmethine) -propanone:
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- (vinyl phenyl) -acrylketone 0.01mol and diethyl malonate 0.012mol, slowly heating, carrying out reflux reaction, and monitoring by TLC until the reaction is finished (40 min);
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- (vinyl phenyl) -3- (ethyl dicarboxylate methine) -acetone. The yield is 81.3%, and the m.p. is 72-74 ℃; and recovering the filtrate to obtain the eutectic solvent. The eutectic solvent was reused at a 1 st yield of 81.1%, a 2 nd yield of 80.8%, a 3 rd yield of 80.6%, a 4 th yield of 80.2%, and a 5 th yield of 80%.
The structural characterization data for the product is:
IR(KBr)ν:2989,2885,1685,1634(C=O),1589,1453(Ar-H),1432(-CH2),1375(-CH3);
1HNMR(400MHz,DMSO-d6)δ:7.69(d,1H,=CH),7.46-7.67(d,2H,Ph-H),7.45(d,2H,Ph-H),7.14-7.18(m,1H,Ph-H),7.11(d,1H,=CH),4.98(s,2H,Fe-H),4.62(s,2H,Fe-H),4.25(s,5H,Fe-H),4.06-4.11(q,2H,-COOCH2),3.55-3.80(m,2H,-CH),2.65-2.66(d,2H,-OCH2),1.29-1.32(t,3H,-CH2CH3);
13CNMR(100MHz,DMSO-d6):193.14,172.11,140.90,136.41,128.97,127.15,126.58,80.73,72.70,69.65,62.03,54.93,43.66,27.45,15.27.
Claims (9)
1. a process for the preparation of 1-ferrocenyl-3-aryl-3- (ethylcarbamoylmethine) -propanone comprising the steps of:
the 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate) methine-acetone is obtained by the Michael addition reaction of 1-ferrocenyl-3-aryl-acrylketone and ethyl acetoacetate under the catalysis of choline chloride/urea eutectic solvent.
2. The method according to claim 1, wherein choline chloride and urea are dissolved by heating in a molar ratio of 1:2 to obtain a eutectic solvent.
3. The method of claim 1, wherein the molar ratio of choline chloride, urea, 1-ferrocenyl-3-aryl-propenone, and diethyl malonate is 1:2:0.01 (0.01-0.013).
4. The method of claim 1, wherein the aryl group is a phenyl group, a halophenyl group, a methylphenyl group, an ethylphenyl group, a propylphenyl group, a methoxyphenyl group, a nitrophenyl group, a hydroxyphenyl group, an aminophenyl group, a five-membered heterocyclic group, or a six-membered heterocyclic group.
5. The method of claim 4, 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.
6. The method of claim 4, wherein the nitrophenyl group 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.
7. The method of claim 4, wherein said five-membered heterocyclic group is furyl or thienyl; the six-membered heterocyclic group is pyridyl.
8. The method of claim 1, 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 1-ferrocenyl-3-aryl-acrylketone C mol and ethyl acetoacetate D mol, slowly heating, carrying out reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is complete, wherein the reaction time is 20-40 min; wherein A, B, C, D =1:2:0.01 (0.01-0.013).
9. The method of claim 8, wherein after the reaction is finished, the reaction liquid is cooled to room temperature, a small amount of water is added, solid is immediately separated out, a filter cake is obtained by suction filtration, and the filter cake is washed by water and dried in vacuum to obtain 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate methine) -acetone; and recovering the filtrate to obtain the eutectic solvent.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911155156.6A CN110804076A (en) | 2019-11-22 | 2019-11-22 | Method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methine) -acetone |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911155156.6A CN110804076A (en) | 2019-11-22 | 2019-11-22 | Method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methine) -acetone |
Publications (1)
Publication Number | Publication Date |
---|---|
CN110804076A true CN110804076A (en) | 2020-02-18 |
Family
ID=69491147
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201911155156.6A Pending CN110804076A (en) | 2019-11-22 | 2019-11-22 | Method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methine) -acetone |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110804076A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114047180A (en) * | 2021-09-28 | 2022-02-15 | 陕西科技大学 | Method for detecting chromate ions and dichromate ions |
-
2019
- 2019-11-22 CN CN201911155156.6A patent/CN110804076A/en active Pending
Non-Patent Citations (4)
Title |
---|
SCOTT T. HANDY: "Deep Eutectic Solvents in Organic Synthesis", 《IONIC LIQUIDS - CURRENT STATE OF THE ART》 * |
URMILADEVI NARAD YADAV等: "Synergistic effect of ultrasound and deep eutectic solvent choline chloride–urea as versatile catalyst for rapid synthesis of β-functionalized ketonic derivatives", 《JOURNAL OF MOLECULAR LIQUIDS》 * |
ZHI-LIANG SHEN等: "MICROWAVE-ASSISTED MICHAEL ADDITION OF DIETHYL MALONATE WITH FERROCENYL SUBSTITUTED CHALCONES UNDER SOLVENT-FREE CONDITIONS", 《SYNTHETIC COMMUNICATIONS》 * |
严楠等: "低共熔溶剂中新型螺环吲哚衍生物的绿色合成", 《有机化学》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114047180A (en) * | 2021-09-28 | 2022-02-15 | 陕西科技大学 | Method for detecting chromate ions and dichromate ions |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH07508015A (en) | Synthesis of 1,4,7-triazacyclononane derivatives | |
CN111285768B (en) | Polyion liquid type chiral copper amino acid catalyst and preparation method thereof | |
CN111229311B (en) | Supported imidazole ionic liquid catalyst and method for synthesizing 2-amino-3-cyano-4H-pyran compounds | |
CN104876971B (en) | Based on Co(Ⅱ)Metal organic frame and preparation method and application | |
CN110804076A (en) | Method for preparing 1-ferrocenyl-3-aryl-3- (ethyl dicarboxylate group methine) -acetone | |
CN112264105B (en) | Supported palladium catalyst for synthesis of substituted ketone and bisphenol F | |
CN113549062A (en) | Chiral quaternary ammonium salt phase transfer catalyst with high steric hindrance derived from cinchona alkaloid and synthesis method thereof | |
CN110724169B (en) | Method for preparing 1-ferrocenyl-3-aryl-3-diacetyl methylene-acetone | |
CN115572272B (en) | Preparation method of febuxostat and aldehyde ester intermediate thereof | |
CN110394190A (en) | Triazine radical cup [4] aromatic polymer loaded palladium catalyst and preparation method and application rich in nitrogen | |
CN107715909B (en) | Pentaerythritol-supported proline catalyst and preparation method and application thereof | |
CN108129424B (en) | Method for catalyzing decarbonylation reaction of furfural derivatives by using bidentate phosphine ligand polymer supported palladium catalyst | |
CN107721936B (en) | Method for aqueous phase synthesis of 3, 4-dihydropyrimidine-2-ketone compounds | |
CN110627840B (en) | Method for preparing 1-ferrocenyl-3-aryl-3- (1-acetyl-1-ethoxycarbonyl) methinone | |
CN112812066B (en) | Synthesis method of dihydropyrimidinone compound | |
KR20130133315A (en) | Method for preparing isosorbide from sorbitol using water-compatible lewis acid | |
CN112457175A (en) | Method for preparing 1, 3-dibenzyloxy-2-acetone | |
CN111217862A (en) | Preparation method of 4-aryl-6-ferrocenyl-3, 4-dihydropyrimidine-2 (1H) -ketone | |
CN109665967B (en) | Ligand for asymmetric epoxidation reaction of indene compounds and preparation method and application thereof | |
CN103387543A (en) | Synthesis method of tetrahydropyrazolone derivative | |
EA036663B1 (en) | Method for preparing azoxystrobin | |
CN109942480B (en) | Synthetic method of aromatic ring indole-5-alcohol compound | |
CN107602316B (en) | Method for selectively synthesizing allyl sulfone compound | |
CN106966877B (en) | 1, 4-dicarbonyl compound and preparation method thereof | |
CN105801478A (en) | Method for preparing 2-aryl quinoline by cyclic ether compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200218 |
|
RJ01 | Rejection of invention patent application after publication |