CN112898128B - Synthesis method of russula rupestris ant pheromone component 3-ethyl-4-methylpentanol - Google Patents
Synthesis method of russula rupestris ant pheromone component 3-ethyl-4-methylpentanol Download PDFInfo
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Abstract
The invention discloses a method for synthesizing a russulam ant pheromone component 3-ethyl-4-methylpentanol, which comprises the following steps: under the catalysis of supported fluorine salt formed by a supported substance and fluorine salt, ethoxyformyl methylene triphenylphosphine and 2-methyl-3-pentanone are heated to react, and after the reaction is finished, 3-ethyl-4-methyl-2-ethyl pentenoate is obtained through purification; dissolving the obtained 3-ethyl-4-methyl-2-ethyl pentenoate in an organic solvent, reacting with lithium aluminum hydride under the catalysis of Lewis acid, and treating after the reaction is complete to obtain 3-ethyl-4-methyl amyl alcohol; the synthesis method has the advantages of low cost and easy obtainment of the adopted synthesis raw materials, simple reaction conditions, few reaction steps, simple operation, low production cost, high production efficiency, high yield and high product purity, and is suitable for large-scale production.
Description
Technical Field
The invention belongs to the technical field of chemical production, and particularly relates to a method for synthesizing a russulam ant pheromone component 3-ethyl-4-methylpentanol.
Background
The Formica rufa (Formica lufa) is widely distributed in China, has a large quantity, belongs to hymenoptera insects, is beneficial insects in forests, and is a good edible insect and a good medicinal insect. As early as 3000 years, it is recorded that the monarch in the Zhou dynasty has eaten ants, and has great benefits for curing diseases, building body and prolonging life. The larvae of the pests such as pine moth, pine leaf bee, tsetse, larch, she Songyin leaf rollers, spruce yellow leaf rollers and the like are main pests of She Songshe parts and cones, and the red brown forest ants can prey on the pests, thus having great protection effect on forests. The russular ant also contains abundant proteins and amino acids necessary for human bodies, contains various vitamins and various microelements, contains high content of zinc, and formic acid and the like which are difficult to synthesize artificially, and has the functions of resisting aging, rheumatism and tumors, so that the research and development of the russular ant have important significance.
The red brown ants survive in a social mode, and the number of the ants can reach up to 50 ten thousand; few ants in the ant colony are responsible for spawning deep in the nest after being caught by workers. Almost all members of the ant colony are workers and they are responsible for the work of the ant colony: cares young ants, repairs and expands nest, forges food when going out, and guards nest entrance; the actions of ants are consistent and orderly, which requires pheromones secreted by the red brown ants themselves; a very important component in the semiochemicals within the family of the russian ants is 3-ethyl-4-methylpentanol, cas No. 38514-13-5.
The synthesized high-quality 3-ethyl-4-methyl amyl alcohol which is an important component of the communication pheromone can be used for researching various habits of the rufous and further developing the economic effect of the rufous.
The synthesis of 3-ethyl-4-methylpentanol is rarely reported, and the synthetic route in document [ Chemistry of Natural Comp ounds,2019,55 (5), 987 ] is as follows:
under the catalysis of 5-tantalum chloride/triisopropyl phosphite, n-butyl magnesium bromide reacts with propylene under high pressure at-68 ℃, then reacts with dry ice, and acidizes to obtain 3-ethyl-4-methyl pentanoic acid, or the 3-ethyl-4-methyl pentanol can be obtained through the reduction reaction of lithium aluminum hydride. The synthesis method involves operations such as high pressure, ultralow temperature, strict anhydrous and the like, has complex process and high equipment requirement, and is difficult to produce in a large scale, so that the search for a more ideal synthesis process is indispensable.
In view of the favorable economic effect of the russian ants, pheromones are needed to be synthesized to strengthen the study on the life habits of the russian ants; therefore, it is very significant to find a novel synthesis method to realize the industrial production of the russian ant communication pheromone 3-ethyl-4-methylpentanol; this requires development of a good production process to enable industrial production of the ac pheromone.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a method for synthesizing the russian ant pheromone component 3-ethyl-4-methylpentanol, which has the advantages of low cost and easy acquisition of synthesis raw materials, simple reaction conditions, few reaction steps, simple operation, low production cost, high production efficiency, high yield and high product purity, and is suitable for large-scale production.
In order to achieve the technical purpose and the technical effect, the invention is realized by the following technical scheme:
the synthesis method of the russian ant pheromone component 3-ethyl-4-methylpentanol comprises the following steps:
step (1), under the catalysis of supported fluorine salt formed by a supported object and fluorine salt, carrying out a reaction between ethoxyformylmethylene triphenylphosphine shown in a formula (I) and 2-methyl-3-pentanone shown in a formula (II), and purifying after the reaction is finished to obtain 3-ethyl-4-methyl-2-ethyl pentenoate shown in a formula (III);
dissolving the ethyl 3-ethyl-4-methyl-2-pentenoate obtained in the step (1) in an organic solvent, reacting with lithium aluminum hydride under the catalysis of Lewis acid, and treating after the reaction is complete to obtain 3-ethyl-4-methylpentanol shown in a formula (IV);
the synthetic route is as follows:
further, the reaction temperature in the step (1) is 120-150 ℃.
Further, the fluorine salt loaded in the step (1) is obtained by mixing a load with the fluorine salt and then activating the mixture; wherein the load is at least one of alumina, ferric oxide, diatomite, molecular sieve, kaolin, active carbon, zirconia, zinc oxide, magnesia and silicon oxide; wherein the fluoride salt is at least one of sodium fluoride, potassium fluoride, ammonium fluoride, lithium fluoride, aluminum fluoride, magnesium fluoride, cesium fluoride, strontium fluoride, lanthanum fluoride, and gallium fluoride.
Further, the mass ratio of the load in the load fluorine salt to the fluorine salt is 1-2: 20.
further, in the step (1), the molar ratio of the 2-methyl-3-pentanone, the ethoxyformylmethylene triphenylphosphine and the fluoride salt is 1:1 to 1.5:0.1 to 0.5.
Further, the reaction temperature in the step (2) is-20-80 ℃.
Further, the organic solvent in the step (2) is at least one of tetrahydrofuran, methyltetrahydrofuran, isopropyl ether, ethylene glycol dimethyl ether, methyl tertiary butyl ether, toluene, 1, 4-dioxane and methyl cyclopentyl ether.
Further, the lewis acid in the step (2) is at least one of aluminum trichloride, ferric chloride, boron trifluoride diethyl ether, indium trichloride, zinc chloride, calcium chloride, nickel bromide, phosphorus oxychloride, copper triflate, indium triflate, silver triflate, aluminum triflate and nickel triflate.
Further, in the step (2), the molar ratio of the 3-ethyl-4-methyl-2-ethyl pentenoate to the lithium aluminum hydride to the Lewis acid is 1: 1-2: 1 to 5.0.
Further, in the step (2), the material treatment process after the reaction is as follows: extracting and combining organic phases in the reacted materials, washing, drying, concentrating the organic phases, and purifying the concentrated residues.
The beneficial effects of the invention are as follows:
the synthetic method of the invention uses ethoxyformyl methylene triphenylphosphine and 2-methyl-3-pentanone as raw materials, and wittig reaction can smoothly occur under the catalysis of supported fluorine salt to obtain 3-ethyl-4-methyl-2-ethyl pentenoate; the 3-ethyl-4-methyl-2-pentenoic acid ethyl ester is subjected to Lewis acid catalysis, and the lithium aluminum hydride is used for reducing ester groups and carbon-carbon double bonds by a one-step method to obtain a target product 3-ethyl-4-methyl amyl alcohol. The invention is a new synthetic method, the involved synthetic raw materials are cheap and easy to obtain, the reaction conditions are simple, the reaction steps are few, the operation is simple, the production cost is low, the production efficiency is high, the yield is high, the purity of the obtained product is high, the product is suitable for mass production, and the market demand is satisfied.
Detailed Description
The following description of the embodiments of the present invention will be made more apparent and fully by reference to the accompanying drawings, in which it is shown, by way of illustration, only some, but not all embodiments of the invention. 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 discloses a method for synthesizing a russulam ant pheromone component 3-ethyl-4-methylpentanol, which comprises the following steps:
step (1), under the catalysis of supported fluorine salt formed by a supported object and fluorine salt, carrying out a reaction between ethoxyformylmethylene triphenylphosphine shown in a formula (I) and 2-methyl-3-pentanone shown in a formula (II), and purifying after the reaction is finished to obtain 3-ethyl-4-methyl-2-ethyl pentenoate shown in a formula (III);
dissolving the ethyl 3-ethyl-4-methyl-2-pentenoate obtained in the step (1) in an organic solvent, reacting with lithium aluminum hydride under the catalysis of Lewis acid, and treating after the reaction is complete to obtain 3-ethyl-4-methylpentanol shown in a formula (IV); specifically, in the step (2), the lithium aluminum hydride is dissolved in an organic solvent, and then the mixed solution of the lithium aluminum hydride and the organic solvent is mixed with 3-ethyl-4-methyl-2-ethyl pentenoate for reaction;
the synthetic route is as follows:
in the above synthesis method, the reaction temperature in the step (1) is 120 to 150 ℃.
In the synthesis method, the supported fluorine salt in the step (1) is obtained by mixing a supported substance with the fluorine salt and then activating the mixture; wherein the load is at least one of alumina, ferric oxide, diatomite, molecular sieve, kaolin, active carbon, zirconia, zinc oxide, magnesia and silicon oxide; wherein the fluoride salt is at least one of sodium fluoride, potassium fluoride, ammonium fluoride, lithium fluoride, aluminum fluoride, magnesium fluoride, cesium fluoride, strontium fluoride, lanthanum fluoride, and gallium fluoride.
The mass ratio of the load in the load fluorine salt to the fluorine salt is 1-2: 20.
in the above synthetic method, the molar ratio of the 2-methyl-3-pentanone, the ethoxyformylmethylene triphenylphosphine and the fluoride salt in the step (1) is 1:1 to 1.5:0.1 to 0.5.
In the above synthesis method, the reaction temperature in the step (2) is-20 to 80 ℃.
Further, the organic solvent in the step (2) is at least one of tetrahydrofuran, methyltetrahydrofuran, isopropyl ether, ethylene glycol dimethyl ether, methyl tertiary butyl ether, toluene, 1, 4-dioxane and methyl cyclopentyl ether.
In the above synthetic method, the lewis acid in step (2) is at least one of aluminum trichloride, ferric chloride, boron trifluoride diethyl ether, indium trichloride, zinc chloride, calcium chloride, nickel bromide, phosphorus oxychloride, copper triflate, indium triflate, silver triflate, aluminum triflate, nickel triflate.
In the above synthesis method, the molar ratio of the 3-ethyl-4-methyl-2-pentenoic acid ethyl ester, the lithium aluminum hydride and the Lewis acid in the step (2) is 1: 1-2: 1 to 5.0.
In the step (2) of the synthesis method, the material treatment process after the reaction is as follows: extracting and combining organic phases in the reacted materials, washing, drying, concentrating the organic phases, and purifying the concentrated residues.
Example 1
1.2g of potassium fluoride (20 mmol) is dissolved in 10mL of water, then 20g of alumina is added, stirred uniformly and placed at 120 ℃ for activation for 2 hours; cooling to obtain a supported fluorine salt, transferring the supported fluorine salt into a thick-wall pressure-resistant bottle, adding 5g of 2-methyl-3-pentanone (50 mmol) and 20.9g of ethoxyformyl methylene triphenylphosphine (60 mmol), fully and uniformly stirring, and placing in an oil bath at 150 ℃ for reacting for 1 hour; then, cooling to room temperature, transferring the reacted mixture into a chromatographic column filled with silica gel, and performing column chromatography purification (petroleum ether: ethyl acetate=30:1 as eluent) to obtain 8g of 3-ethyl-4-methyl-2-pentenoic acid ethyl ester (yield is 94%);
a reaction flask was taken, to which were added 8g of the obtained ethyl 3-ethyl-4-methyl-2-pentenoate (47.1 mmol) and 100mL of tetrahydrofuran, cooled to 0℃and 13.3g of aluminum trichloride (100 mmol) was further added and stirred for 30 minutes; 80mL of lithium aluminum tetrahydroide-tetrahydrofuran solution (80 mmol, 1M) was added dropwise, and the temperature was raised to 30℃after the completion of the dropwise addition and the reaction was carried out overnight. Then, cooling with ice water, dropwise adding cold water until no gas is generated, regulating the solution to be clear with hydrochloric acid, extracting with chloroform, combining organic phases, washing with water, drying with sodium sulfate, concentrating, and purifying the residue by column chromatography (200 mesh silica gel is filled in a chromatographic column, and petroleum ether is adopted as eluent: ethyl acetate=10:1) to obtain 5.8g of 3-ethyl-4-methylpentanol, wherein the yield is 95%; the nuclear magnetic resonance results were: 1H NMR (400 MHz, CDCl 3): delta 0.81-0.99 (m, 9H), 1.12-1.85 (m, 7H), 3.66 (t, J=7.2 Hz, 2H); 13C NMR (100 MHz, CDCl 3): delta 12.01,18.79,19.51,23.42,29.16,33.36,42.21,61.88.
Example 2
1.5g of cesium fluoride (10 mmol) is dissolved in 10mL of water, 20g of diatomite is added, and the mixture is stirred uniformly and placed at 120 ℃ for activation for 2 hours; cooling to obtain a supported fluorine salt; transferring the fluorine-loaded salt into a thick-wall pressure-resistant bottle, adding 5g of 2-methyl-3-pentanone (50 mmol) and 20.9g of ethoxyformyl methylene triphenylphosphine (60 mmol), fully and uniformly stirring, and placing in an oil bath at 140 ℃ for reaction for 2 hours; then cooling to room temperature, transferring the reacted mixture into a chromatographic column filled with silica gel, and performing column chromatography purification (petroleum ether: ethyl acetate=30:1 as eluent) to obtain 8.5g (yield is 95%) of 3-ethyl-4-methyl-2-pentenoic acid ethyl ester;
a reaction flask was taken, 43.8g of nickel bromide (200 mmol) and 250mL of tetrahydrofuran were added thereto, cooled to 0℃and 100mL of a solution of lithium aluminum hydride-tetrahydrofuran (100 mmol, 1M) was added dropwise thereto, and stirred for 1 hour; 8.5g of the resulting ethyl 3-ethyl-4-methyl-2-pentenoate (50 mmol) were dissolved in 100mL of tetrahydrofuran; dropwise adding a mixed solution of 3-ethyl-4-methyl-2-ethyl pentenoate and tetrahydrofuran into a reaction bottle, and then heating to 50 ℃ for reaction for 1 hour; cooling with ice water, adding cold water dropwise until no gas is generated, regulating hydrochloric acid to clarify the solution, concentrating to remove solvent, extracting with chloroform, mixing organic phases, washing with water, drying with sodium sulfate, concentrating, and purifying the residue by column chromatography (200 mesh silica gel is filled in the column, and the eluent is petroleum ether: ethyl acetate=10:1), to obtain 6.4g of 3-ethyl-4-methylpentanol with 98% yield; nuclear magnetic resonance results: the 1HNMR and 13C NMR detection data of the product were identical to those of example 1.
Example 3
1.6g of magnesium fluoride (25 mmol) is dissolved in 10mL of water, 20g of kaolin is added, the mixture is stirred uniformly and is placed at 120 ℃ for activation for 2 hours; cooling to obtain a supported fluorine salt, transferring the supported fluorine salt into a thick-wall pressure-resistant bottle, adding 5g of 2-methyl-3-pentanone (50 mmol) and 20.9g of ethoxyformyl methylene triphenylphosphine (60 mmol), fully and uniformly stirring, and placing in an oil bath at 160 ℃ for reaction for 3 hours. Then, cooling to room temperature, transferring the reacted mixture into a chromatographic column filled with silica gel, and performing column chromatography purification (petroleum ether is used as eluent: ethyl acetate=30:1) to obtain 7.8g of 3-ethyl-4-methyl-2-ethyl pentenoate, wherein the yield is 92%;
a reaction flask was taken, 7.8g of the obtained ethyl 3-ethyl-4-methyl-2-pentenoate 45.9 mmol) and 100mL of tetrahydrofuran were added to the reaction flask, cooled to-15℃and 75mL of a solution of lithium aluminum hydride-tetrahydrofuran (75 mmol, 1M) was added dropwise thereto and reacted for 1 hour with stirring; maintaining the temperature at-15 ℃, dropwise adding a mixed solution of phosphorus oxychloride (11.5 g,75 mmol) and tetrahydrofuran (150 mL), and gradually heating to micro-reflux reaction for 1 hour; cooling with ice water, adding cold water dropwise until no gas is generated, regulating hydrochloric acid to clarify the solution, concentrating to remove solvent, extracting with chloroform, mixing organic phases, washing with water, drying with sodium sulfate, concentrating, and purifying the residue by column chromatography (200 mesh silica gel is filled in the column, and the eluent is petroleum ether: ethyl acetate=10:1), to obtain 5.9g of 3-ethyl-4-methylpentanol with a yield of 95%; nuclear magnetic resonance results: the 1HNMR and 13C NMR detection data of the product were identical to those of example 1.
The foregoing description is only illustrative of the present invention and is not intended to limit the scope of the invention, and all modifications or equivalent arrangements using the teachings of this invention, or direct or indirect application in other related arts, are included within the scope of this invention.
Claims (8)
1. The synthesis method of the russian ant pheromone component 3-ethyl-4-methylpentanol is characterized by comprising the following steps of:
step (1), under the catalysis of supported fluorine salt formed by a supported object and fluorine salt, carrying out a reaction between ethoxyformylmethylene triphenylphosphine shown in a formula (I) and 2-methyl-3-pentanone shown in a formula (II), and purifying after the reaction is finished to obtain 3-ethyl-4-methyl-2-ethyl pentenoate shown in a formula (III); wherein the loading fluorine salt is obtained by mixing a loading substance with fluorine salt and activating the mixture; wherein the load is at least one of alumina, ferric oxide, diatomite, molecular sieve, kaolin, active carbon, zirconia, zinc oxide, magnesia and silicon oxide; wherein the fluoride salt is at least one of sodium fluoride, potassium fluoride, ammonium fluoride, lithium fluoride, aluminum fluoride, magnesium fluoride, cesium fluoride, strontium fluoride, lanthanum fluoride and gallium fluoride;
dissolving the ethyl 3-ethyl-4-methyl-2-pentenoate obtained in the step (1) in an organic solvent, reacting with lithium aluminum hydride under the catalysis of Lewis acid, and treating after the reaction is complete to obtain 3-ethyl-4-methylpentanol shown in a formula (IV); wherein the Lewis acid is at least one of aluminum trichloride, ferric chloride, boron trifluoride diethyl ether, indium trichloride, zinc chloride, calcium chloride, nickel bromide, phosphorus oxychloride, copper trifluoromethane sulfonate, indium trifluoromethane sulfonate, silver trifluoromethane sulfonate, aluminum trifluoromethane sulfonate and nickel trifluoromethane sulfonate;
the synthetic route is as follows:
2. the method for synthesizing the russian ant pheromone component 3-ethyl-4-methylpentanol according to claim 1, wherein the reaction temperature of the step (1) is 120-150 ℃.
3. The method for synthesizing the russian ant pheromone component 3-ethyl-4-methylpentanol according to claim 1, wherein the mass ratio of the load in the load fluorine salt to the fluorine salt is 1-2: 20.
4. the method for synthesizing the russian pheromone component 3-ethyl-4-methylpentanol according to claim 1, wherein in the step (1), the molar ratio of the 2-methyl-3-pentanone to the ethoxyformylmethylene triphenylphosphine to the fluoride salt is 1:1 to 1.5:0.1 to 0.5.
5. The method for synthesizing the russian ant pheromone component 3-ethyl-4-methylpentanol according to claim 1, wherein the reaction temperature of the step (2) is-20-80 ℃.
6. The method for synthesizing the russet ant pheromone component 3-ethyl-4-methylpentanol according to claim 1, wherein the organic solvent in the step (2) is at least one of tetrahydrofuran, methyltetrahydrofuran, isopropyl ether, ethylene glycol dimethyl ether, methyl tertiary butyl ether, toluene, 1, 4-dioxane and methyl cyclopentyl ether.
7. The method for synthesizing the russulam ant pheromone component 3-ethyl-4-methylpentanol according to claim 1, wherein in the step (2), the molar ratio of the ethyl 3-ethyl-4-methyl-2-pentenoate, lithium aluminum hydride and lewis acid is 1: 1-2: 1 to 5.0.
8. The method for synthesizing the russian ant pheromone component 3-ethyl-4-methylpentanol according to claim 1, wherein in the step (2), the material treatment process after the reaction is as follows: extracting and combining organic phases in the reacted materials, washing, drying, concentrating the organic phases, and purifying the concentrated residues.
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