CN112898128A - Method for synthesizing 3-ethyl-4-methylpentanol as pheromone component of limonum aureum - Google Patents
Method for synthesizing 3-ethyl-4-methylpentanol as pheromone component of limonum aureum Download PDFInfo
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- CN112898128A CN112898128A CN202110180552.5A CN202110180552A CN112898128A CN 112898128 A CN112898128 A CN 112898128A CN 202110180552 A CN202110180552 A CN 202110180552A CN 112898128 A CN112898128 A CN 112898128A
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- C07—ORGANIC CHEMISTRY
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention discloses a method for synthesizing a 3-ethyl-4-methylpentanol as a pheromone component of a limonum aureum, which comprises the following steps: under the catalytic action of a load villiaumite formed by a load and villiaumite, heating carbethoxymethylene triphenylphosphine and 2-methyl-3-pentanone for reaction, and purifying after the reaction is finished to obtain 3-ethyl-4-methyl-2-pentenoic acid ethyl ester; dissolving the obtained 3-ethyl-4-methyl-2-pentenoic acid ethyl ester in an organic solvent, reacting with lithium aluminum hydride under the catalysis of Lewis acid, and treating after full reaction to obtain 3-ethyl-4-methylpentanol; the synthetic raw materials adopted by the synthetic method 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 product purity is high, and the method 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 3-ethyl-4-methylpentanol as a pheromone component of a limonum ant.
Background
The Formica fusca (Formica lufa) is widely distributed and large in quantity in China, belongs to insects in the formitera formicidae, is not only a beneficial insect in a forest, but also a good edible insect and a good medicinal insect. As early as 3000 years ago, it was recorded that the Zhou dynasty emperor had eaten ants, which is very good for curing diseases, building body and prolonging life. The larvae of pests such as pine moth, pine leaf wasp, pine ruler wok, cryptolepis falcata, spruce yellow cabbage moth and the like are main pests of leaf parts and cones of the larch, and the limonum ants can prey on the pests and have great protection effect on forests. The brown forest ant also contains rich protein, amino acid necessary for human body, multiple vitamins, multiple trace elements, high-content zinc, formic acid which is difficult to synthesize artificially and the like, and has the functions of resisting aging, rheumatism and tumors, so that the research and development of the brown forest ant have important significance.
The brown forest ants live in a colony mode, and the number of the ants can be as large as 50 thousands; a few ants in the ant colony are responsible for laying eggs in the deep part of the nest, and workers care for the ants. Almost all members of the ant colony are worker ants, which are responsible for the various tasks in the ant colony: caring young ants, repairing and expanding nest, foraging and watching the entrance of the nest; the actions of ants are consistent and well-ordered, which requires pheromones secreted by the red brown forest ants; a very important component of the consensus pheromone within the family of the red brown ant is 3-ethyl-4-methylpentanol, Cas number 38514-13-5.
The high-quality 3-ethyl-4-methylpentanol which is an important component of the communication pheromone is synthesized, and can be used for researching various habits of the red brown forest ants and further developing the economic action of the red brown forest ants.
The synthesis of 3-ethyl-4-methylpentanol is rarely reported, and the synthetic route in the literature [ Chemistry of Natural Comp outputs, 2019,55(5),987 ] is as follows:
reacting n-butyl magnesium bromide with propylene under high pressure at-68 ℃ under the catalysis of 5-tantalum chloride/triisopropyl phosphite ester, reacting with dry ice, and acidifying to obtain 3-ethyl-4-methyl pentanoic acid, or synthesizing to obtain 3-ethyl-4-methyl pentanol through lithium aluminum hydride reduction reaction. The synthesis method relates to operations of high pressure, ultralow temperature, strict anhydrous and the like, has complex process and high equipment requirement, and is difficult to amplify production, so that the search for a more ideal synthesis process is indispensable.
In view of the economic benefits of the brown forest ant, pheromones need to be synthesized to enhance the study on the life habits of the brown forest ant; therefore, it is very meaningful to find a novel synthetic method for realizing the industrial production of the 3-ethyl-4-methylpentanol of the alternaria alternata communication pheromone; this requires the development of a good production process to enable the commercial production of the communicating pheromone.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a synthesis method of a 3-ethyl-4-methylpentanol as a pheromone component of a limonum ant, which adopts cheap and easily-obtained synthesis raw materials, has 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 achieve the technical effect, the invention is realized by the following technical scheme:
the synthesis method of the 3-ethyl-4-methylpentanol as the pheromone component of the limonum aureum comprises the following steps:
heating and reacting ethoxycarbonyl methylene triphenylphosphine shown in a formula (I) and 2-methyl-3-pentanone shown in a formula (II) under the catalytic action of a load fluorine salt formed by a load and the fluorine salt, and purifying after the reaction is finished to obtain 3-ethyl-4-methyl-2-pentenoic acid ethyl ester shown in a formula (III);
step (2), 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 full reaction to obtain 3-ethyl-4-methylpentanol shown in a formula (IV);
the synthetic route is as follows:
further, the reaction temperature of the step (1) is 120-150 ℃.
Further, the loaded fluorine salt in the step (1) is obtained by mixing a load and fluorine salt and then activating; wherein the load is at least one of alumina, ferric oxide, diatomite, molecular sieve, kaolin, active carbon, zirconia, zinc oxide, magnesia and silica; the fluorine 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 loading substance in the loaded villiaumite to the villiaumite is 1-2: 20.
further, in the step (1), the molar ratio of the 2-methyl-3-pentanone to the carbethoxymethylene triphenylphosphine to the fluorine salt is 1: 1-1.5: 0.1 to 0.5.
Further, the reaction temperature in the step (2) is-20-80 ℃.
Further, the organic solvent in step (2) is at least one of tetrahydrofuran, methyltetrahydrofuran, isopropyl ether, ethylene glycol dimethyl ether, methyl tert-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 etherate, indium trichloride, zinc chloride, calcium chloride, nickel bromide, phosphorus oxychloride, copper trifluoromethanesulfonate, indium trifluoromethanesulfonate, silver trifluoromethanesulfonate, aluminum trifluoromethanesulfonate and nickel trifluoromethanesulfonate.
Further, in the step (2), the molar ratio of the 3-ethyl-4-methyl-2-pentenoic acid ethyl ester 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: and extracting and combining organic phases in the reacted materials, washing, drying and concentrating the organic phases, and purifying the concentrated residues.
The invention has the beneficial effects that:
according to the synthesis method, carbethoxy methylene triphenylphosphine and 2-methyl-3-pentanone are used as raw materials, and a Wittig reaction can be smoothly carried out under the catalytic action of a load villaumite to obtain 3-ethyl-4-methyl-2-ethyl pentenoate; the 3-ethyl-4-methyl-2-ethyl pentenoate reduces ester groups and carbon-carbon double bonds by a one-step method of lithium aluminum hydride under the catalysis of Lewis acid to obtain a target product, namely 3-ethyl-4-methylpentanol. The invention is a new synthesis method, and the related synthesis 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, and the method can be suitable for mass production and meet the market demand.
Detailed Description
The technical solutions in the present invention will be described clearly and completely with reference to specific embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The synthesis method of the brown forest ant pheromone component 3-ethyl-4-methylpentanol comprises the following steps:
heating and reacting ethoxycarbonyl methylene triphenylphosphine shown in a formula (I) and 2-methyl-3-pentanone shown in a formula (II) under the catalytic action of a load fluorine salt formed by a load and the fluorine salt, and purifying after the reaction is finished to obtain 3-ethyl-4-methyl-2-pentenoic acid ethyl ester shown in a formula (III);
step (2), 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 full reaction to obtain 3-ethyl-4-methylpentanol shown in a formula (IV); specifically, in the step (2), the lithium aluminum hydride is dissolved in the organic solvent, and then the mixed solution of the lithium aluminum hydride and the organic solvent is mixed with ethyl 3-ethyl-4-methyl-2-pentenoate for reaction;
the synthetic route is as follows:
in the synthesis method, the reaction temperature in the step (1) is 120-150 ℃.
In the synthesis method, the loaded villaumite in the step (1) is obtained by mixing a loaded substance and villaumite and then activating; wherein the load is at least one of alumina, ferric oxide, diatomite, molecular sieve, kaolin, active carbon, zirconia, zinc oxide, magnesia and silica; the fluorine 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 loading substance in the loaded villiaumite to the villiaumite is 1-2: 20.
in the synthesis method, the molar ratio of the 2-methyl-3-pentanone, the carbethoxymethylene triphenylphosphine and the fluorine salt in the step (1) is 1: 1-1.5: 0.1 to 0.5.
In the synthesis method, the reaction temperature in the step (2) is-20-80 ℃.
Further, the organic solvent in step (2) is at least one of tetrahydrofuran, methyltetrahydrofuran, isopropyl ether, ethylene glycol dimethyl ether, methyl tert-butyl ether, toluene, 1, 4-dioxane and methyl cyclopentyl ether.
In the synthesis method, the lewis acid in the step (2) is at least one of aluminum trichloride, ferric chloride, boron trifluoride diethyl etherate, indium trichloride, zinc chloride, calcium chloride, nickel bromide, phosphorus oxychloride, copper trifluoromethanesulfonate, indium trifluoromethanesulfonate, silver trifluoromethanesulfonate, aluminum trifluoromethanesulfonate and nickel trifluoromethanesulfonate.
In the synthesis method, the molar ratio of the ethyl 3-ethyl-4-methyl-2-pentenoate, 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: and extracting and combining organic phases in the reacted materials, washing, drying and concentrating the organic phases, and purifying the concentrated residues.
Example 1
Dissolving 1.2g of potassium fluoride (20mmol) in 10mL of water, then adding 20g of alumina, uniformly stirring, and standing at 120 ℃ for activation for 2 hours; cooling to obtain a load fluorine salt, transferring the load fluorine salt into a thick-wall pressure-resistant bottle, adding 5g of 2-methyl-3-pentanone (50mmol) and 20.9g of ethoxycarbonyl methylene triphenylphosphine (60mmol), fully and uniformly stirring, and placing in an oil bath at 150 ℃ for reacting for 1 hour; then, the reaction mixture was cooled to room temperature, and the reaction mixture was transferred to a column packed with silica gel and purified by column chromatography (eluent petroleum ether: ethyl acetate ═ 30:1) to obtain 8g of ethyl 3-ethyl-4-methyl-2-pentenoate (yield 94%);
taking a reaction bottle, adding 8g of the obtained 3-ethyl-4-methyl-2-pentenoic acid ethyl ester (47.1m mol) and 100mL of tetrahydrofuran, cooling to 0 ℃, adding 13.3g of aluminum trichloride (100mmol), and stirring for 30 minutes; 80mL of a lithium aluminum hydride-tetrahydrofuran solution (80mmol, 1M) was added dropwise, and the temperature was raised to 30 ℃ after the addition was completed, and the reaction was allowed to proceed overnight. Then, cooling with ice water, dropwise adding cold water until no gas is generated, adjusting the solution to be clear with hydrochloric acid, extracting with chloroform, combining organic phases, washing with water, drying with sodium sulfate, concentrating, and purifying with a residue column chromatography (200-mesh silica gel is filled in the column chromatography, and the eluent is petroleum ether and ethyl acetate is 10:1) to obtain 5.8g of 3-ethyl-4-methylpentanol, wherein the yield is 95%; the nuclear magnetic resonance results are as follows: 1H NMR (400MHz, CDCl3): δ 0.81-0.99(m,9H),1.12-1.85(m,7H),3.66(t, J ═ 7.2Hz, 2H); 13C NMR (100MHz, CDCl 3). delta.12.01, 18.79,19.51,23.42,29.16,33.36,42.21, 61.88.
Example 2
Dissolving 1.5g of cesium fluoride (10mmol) in 10mL of water, adding 20g of diatomite, uniformly stirring, and standing at 120 ℃ for activation for 2 hours; cooling to obtain the loaded villiaumite; transferring the load fluorine salt into a thick-wall pressure-resistant bottle, adding 5g of 2-methyl-3-pentanone (50mmol) and 20.9g of carbethoxymethylene triphenylphosphine (60mmol), fully and uniformly stirring, and placing in an oil bath at 140 ℃ for reaction for 2 hours; then, the reaction mixture was cooled to room temperature, and the reaction mixture was transferred to a column packed with silica gel to carry out column chromatography purification (eluent: petroleum ether: ethyl acetate: 30:1) to obtain 8.5g of ethyl 3-ethyl-4-methyl-2-pentenoate (yield 95%);
taking a reaction bottle, adding 43.8g of nickel bromide (200mmol) and 250mL of tetrahydrofuran into the reaction bottle, cooling to 0 ℃, dropwise adding 100mL of lithium aluminum tetrahydrofuran solution (100mmol, 1M), and stirring for 1 hour; 8.5g of the resulting ethyl 3-ethyl-4-methyl-2-pentenoate (50mmol) were dissolved in 100mL of tetrahydrofuran; dropwise adding a mixed solution of ethyl 3-ethyl-4-methyl-2-pentenoate and tetrahydrofuran into a reaction bottle, and then heating to 50 ℃ to react for 1 hour; cooling with ice water, dropwise adding cold water until no gas is generated, adjusting the solution to be clear with hydrochloric acid, concentrating to remove the solvent, extracting with chloroform, combining organic phases, washing with water, drying with sodium sulfate, concentrating, and purifying the residue by column chromatography (the column is filled with 200-mesh silica gel, and the eluent is petroleum ether and ethyl acetate is 10:1) to obtain 6.4g of 3-ethyl-4-methylpentanol with the yield of 98%; nuclear magnetic resonance results: the 1HNMR and 13C NMR data of the product are completely consistent with those of example 1.
Example 3
Dissolving 1.6g of magnesium fluoride (25mmol) in 10mL of water, adding 20g of kaolin, uniformly stirring, and standing at 120 ℃ for activation for 2 hours; and (3) cooling to obtain a supported villiaumite, transferring the supported villiaumite into a thick-wall pressure-resistant bottle, adding 5g of 2-methyl-3-pentanone (50mmol) and 20.9g of ethoxycarbonyl methylene triphenylphosphine (60mmol), fully and uniformly stirring, and placing in an oil bath at 160 ℃ for reaction for 3 hours. Then, the mixture is cooled to room temperature, the mixture after the reaction is transferred to a chromatographic column filled with silica gel for column chromatography purification (an eluent is petroleum ether, ethyl acetate is 30:1), and the product of 7.8g of ethyl 3-ethyl-4-methyl-2-pentenoate is obtained, wherein the yield is 92%;
taking a reaction bottle, adding 7.8g of the obtained 45.9mmol of ethyl 3-ethyl-4-methyl-2-pentenoate) and 100mL of tetrahydrofuran into the reaction bottle, cooling to-15 ℃, dropwise adding 75mL of lithium aluminum hydride-tetrahydrofuran solution (75mmol, 1M), and stirring for reacting for 1 hour; maintaining the temperature at-15 ℃, dropwise adding a mixed solution of phosphorus oxychloride (11.5g, 75mmol) and tetrahydrofuran (150mL), and gradually heating until micro reflux reaction is carried out for 1 hour; cooling with ice water, dropwise adding cold water until no gas is generated, adjusting the solution to be clear with hydrochloric acid, concentrating to remove the solvent, extracting with chloroform, combining organic phases, washing with water, drying with sodium sulfate, concentrating, and purifying the residue by column chromatography (the column is filled with 200-mesh silica gel, and the eluent is petroleum ether and ethyl acetate is 10:1) to obtain 5.9g of 3-ethyl-4-methylpentanol with the yield of 95%; nuclear magnetic resonance results: the 1HNMR and 13C NMR data of the product are completely consistent with those of example 1.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications and equivalents made by the contents of the present invention or directly or indirectly applied to other related technical fields are included in the scope of the present invention.
Claims (10)
1. The method for synthesizing the pheromone component 3-ethyl-4-methylpentanol from the limonum aureum is characterized by comprising the following steps:
heating and reacting ethoxycarbonyl methylene triphenylphosphine shown in a formula (I) and 2-methyl-3-pentanone shown in a formula (II) under the catalytic action of a load fluorine salt formed by a load and the fluorine salt, and purifying after the reaction is finished to obtain 3-ethyl-4-methyl-2-pentenoic acid ethyl ester shown in a formula (III);
step (2), 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 full reaction to obtain 3-ethyl-4-methylpentanol shown in a formula (IV);
the synthetic route is as follows:
2. the method for synthesizing 3-ethyl-4-methylpentanol as a pheromone component of Solenopsis invicta according to claim 1, wherein the reaction temperature in step (1) is 120-150 ℃.
3. The method for synthesizing the pheromone component 3-ethyl-4-methylpentanol of the solenopsis invicta as claimed in claim 1, wherein the loaded villous salt in the step (1) is obtained by mixing the loaded substance with villous 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 silica; the fluorine 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.
4. The method for synthesizing the pheromone component 3-ethyl-4-methylpentanol of the limonum aureum according to claim 3, wherein the mass ratio of the load in the loaded villaumite to the villaumite is 1-2: 20.
5. the method for synthesizing 3-ethyl-4-methylpentanol as pheromone component of Formica rupa Linne as claimed in claim 1, wherein in step (1), the molar ratio of 2-methyl-3-pentanone, carbethoxymethylene triphenylphosphine and villiaumite is 1: 1-1.5: 0.1 to 0.5.
6. The method for synthesizing 3-ethyl-4-methylpentanol as a pheromone component of the Formica rufa of claim 1, wherein the reaction temperature in the step (2) is-20 to 80 ℃.
7. The method of claim 1, wherein the organic solvent used in step (2) is at least one of tetrahydrofuran, methyltetrahydrofuran, isopropyl ether, ethylene glycol dimethyl ether, methyl tert-butyl ether, toluene, 1, 4-dioxane, and methyl cyclopentyl ether.
8. The method for synthesizing 3-ethyl-4-methylpentanol as pheromone component of Formica rupa Linne according to claim 1, wherein the Lewis acid in step (2) is at least one of aluminum trichloride, ferric chloride, boron trifluoride etherate, indium trichloride, zinc chloride, calcium chloride, nickel bromide, phosphorus oxychloride, copper trifluoromethanesulfonate, indium trifluoromethanesulfonate, silver trifluoromethanesulfonate, aluminum trifluoromethanesulfonate, and nickel trifluoromethanesulfonate.
9. The method for synthesizing 3-ethyl-4-methylpentanol as pheromone component of Formica rufa as claimed in claim 1, wherein in the step (2), the molar ratio of ethyl 3-ethyl-4-methyl-2-pentenoate, lithium aluminum hydride and Lewis acid is 1: 1-2: 1 to 5.0.
10. The method for synthesizing 3-ethyl-4-methylpentanol as a pheromone component of Solenopsis invicta according to claim 1, wherein in the step (2), the material treatment process after the reaction is as follows: and extracting and combining organic phases in the reacted materials, washing, drying and concentrating the organic phases, and purifying the concentrated residues.
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