CN105330628B - Method for preparing 4-hydroxy butenolide from keto acid and alkyne - Google Patents
Method for preparing 4-hydroxy butenolide from keto acid and alkyne Download PDFInfo
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- CN105330628B CN105330628B CN201510902662.2A CN201510902662A CN105330628B CN 105330628 B CN105330628 B CN 105330628B CN 201510902662 A CN201510902662 A CN 201510902662A CN 105330628 B CN105330628 B CN 105330628B
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- DUAZKLYNTLDKQK-UHFFFAOYSA-N 5-hydroxy-2(5h)-furanone Chemical compound OC1OC(=O)C=C1 DUAZKLYNTLDKQK-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 150000001345 alkine derivatives Chemical class 0.000 title claims abstract description 17
- 150000004715 keto acids Chemical class 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 239000000047 product Substances 0.000 claims abstract description 13
- 238000004440 column chromatography Methods 0.000 claims abstract description 10
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 239000012043 crude product Substances 0.000 claims abstract description 3
- 230000006837 decompression Effects 0.000 claims abstract description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- VTESCYNPUGSWKG-UHFFFAOYSA-N (4-tert-butylphenyl)hydrazine;hydrochloride Chemical compound [Cl-].CC(C)(C)C1=CC=C(N[NH3+])C=C1 VTESCYNPUGSWKG-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- HFFUXLCRPYMGFM-UHFFFAOYSA-N 1-fluoro-4-[2-(4-fluorophenyl)ethynyl]benzene Chemical group C1=CC(F)=CC=C1C#CC1=CC=C(F)C=C1 HFFUXLCRPYMGFM-UHFFFAOYSA-N 0.000 claims description 4
- OFDOCXDLDQXWIX-UHFFFAOYSA-N 1-methyl-4-[2-(4-methylphenyl)ethynyl]benzene Chemical group C1=CC(C)=CC=C1C#CC1=CC=C(C)C=C1 OFDOCXDLDQXWIX-UHFFFAOYSA-N 0.000 claims description 4
- UASZGGQRDGLTIQ-UHFFFAOYSA-N 2-(4-bromophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Br)C=C1 UASZGGQRDGLTIQ-UHFFFAOYSA-N 0.000 claims description 4
- RSAXVDMWQCQTDT-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Cl)C=C1 RSAXVDMWQCQTDT-UHFFFAOYSA-N 0.000 claims description 4
- YRGDGXWJSRZRAS-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(F)C=C1 YRGDGXWJSRZRAS-UHFFFAOYSA-N 0.000 claims description 4
- UIIIPQVTXBPHTI-UHFFFAOYSA-N 2-(4-methylphenyl)-2-oxoacetic acid Chemical compound CC1=CC=C(C(=O)C(O)=O)C=C1 UIIIPQVTXBPHTI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000003208 petroleum Substances 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010025 steaming Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 238000005575 aldol reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing 4-hydroxy butenolide from keto acid and alkyne, which comprises the following reaction steps: step 1) adding keto acid, alkyne and boron trifluoride diethyl etherate into reaction equipment, taking fluorobenzene as a solvent, and reacting for a period of time at 70 ℃ to obtain a crude product and the solvent; step 2) carrying out decompression operation on the product obtained in the step 1 to evaporate the solvent; and 3) carrying out column chromatography on the product obtained in the step 2 by using an organic solvent to obtain the high-purity 4-hydroxy butenolide. The preparation method is simple and easy to operate, the substrate has wide application range, and the raw materials used in the whole reaction process are cheap and easily available, so that the reaction cost is greatly reduced; in addition, the yield of the preparation method is more than 80%, so that the economic benefit of industrial production is improved.
Description
Technical Field
The invention belongs to the field of synthesis of organic compounds, relates to a preparation method of 4-hydroxy butenolide, and particularly relates to a method for preparing 4-hydroxy butenolide from keto acid and alkyne.
Background
4-hydroxy butenolide is widely present in natural products with biological activity and is also an important organic synthesis intermediate. The molecular formula of the 4-hydroxy butenolide is as follows:
wherein: r1Is aryl or alkyl, R2Is aryl or alkyl, R3Is an aryl group. In recent years, the wide application of 4-hydroxybutenolide in organic synthesis has attracted interest and attention, and the synthesis method of 4-hydroxybutenolide has also made great progress.
In 2002, Kotesswar Rao Yeleswarapu et al, which utilizes intermolecular aldol reaction, takes an alpha-bromocarbonyl compound and carboxylic acid as raw materials, and synthesizes similar compounds by ring closure and oxidation, but the method has certain defects in raw material acquisition. In 2009, Michael Schaers et al prepared similar unsaturated butyrolactones by intermolecular aldol condensation of γ -carbonyl acid esters and aldehydes, and the cumbersome preparation process of the raw materials limited the application range of the reaction. In 2015, Tetsuya Shishido et al synthesized similar unsaturated butyrolactone by high temperature carbonylation using aldehyde, alkyne and CO, but this procedure was complicated, somewhat dangerous and low yielding.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides a method for preparing 4-hydroxy butenolide by using keto acid and alkyne, aiming at solving the problems of complex operation, high requirement on reaction environment and the like in the preparation of 4-hydroxy butenolide, so that the operation of the whole reaction is simple and easy, the reaction cost is reduced, and the economic benefit is improved.
The technical scheme of the invention is as follows: a method for preparing 4-hydroxy butenolide from keto acid and alkyne, which comprises the following reaction equation:
wherein: r1Is aryl or alkyl, R2Is aryl or alkyl, R3Is aryl;
the preparation method comprises the following reaction steps:
step 1) adding keto acid, alkyne and boron trifluoride diethyl etherate into reaction equipment, taking fluorobenzene as a solvent, and reacting for a period of time at 70 ℃ to obtain a crude product and the solvent;
step 2) carrying out decompression operation on the product obtained in the step 1 to evaporate the solvent;
and 3) carrying out column chromatography on the product obtained in the step 2 by using an organic solvent to obtain the high-purity 4-hydroxy butenolide.
Preferably, the ketoacid is any one of benzoylformic acid, p-methylbenzoylformic acid, p-bromobenzoylformic acid, p-chlorobenzoylformic acid or p-fluorobenzoylformic acid.
Preferably, the alkyne is any one of tolane, bis (4-methylphenyl) acetylene or bis (4-fluorophenyl) acetylene.
Preferably, the molar ratio of the keto acid, the alkyne, and the boron trifluoride etherate is 1: 2: 0.3.
preferably, in step 1, the reaction time of the reaction at 70 ℃ is 2 to 5 hours.
Preferably, the organic solvent is a mixture of petroleum ether and ethyl acetate.
Further, the volume ratio of the petroleum ether to the ethyl acetate is 5: 1.
The high-purity 4-hydroxy butenolide obtained by the synthesis reaction can be detected by a nuclear magnetic analyzer (INVOVA400), and the test conditions are as follows: 400MHZ DMSO.
The invention has the advantages that: the preparation method is simple and easy to operate, the substrate has wide application range, and the raw materials used in the whole reaction process are cheap and easily available, so that the reaction cost is greatly reduced; in addition, the yield of the preparation method is more than 80%, so that the economic benefit of industrial production is improved.
Detailed Description
The invention is further described below with reference to the following examples:
the first embodiment is as follows: the 4-hydroxy butenolide is synthesized by the reaction of benzoylformic acid and tolane, and the molecular formula is as follows:
the synthesis reaction comprises the following specific steps:
adding 0.3mmol of benzoylformic acid, 0.6mmol of tolane, 0.09mmol of boron trifluoride diethyl etherate and 2mL of fluorobenzene into a reaction tube in sequence, reacting for 5 hours at 70 ℃, decompressing and evaporating a solvent after the reaction is finished, and then carrying out column chromatography by using a mixture of petroleum ether and ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5:1, and then obtaining a pure product with the yield of 92% and the purity of 98%.
After nuclear magnetic analysis: 1H NMR (400MHz, DMSO). delta.8.69 (s,1H),7.55-7.51(m,2H),7.45-7.32(m,8H),7.25-7.20(m,5H).13C NMR (100MHz, DMSO). delta. 170.2,158.6,137.5,130.5,129.8,129.5,129.3,128.9,128.8,128.6,128.5,128.4,128.3,126.9,125.8,105.7.
Example two: the 4-hydroxy butenolide is synthesized by the reaction of p-methylbenzoyl formic acid and tolane, and the molecular formula is as follows:
the synthesis reaction comprises the following specific steps:
adding 0.3mmol of p-methylbenzoylformic acid, 0.6mmol of tolane, 0.09mmol of boron trifluoride diethyl etherate and 2mL of fluorobenzene into a reaction tube in sequence, reacting for 5 hours at 70 ℃, decompressing and steaming off a solvent after the reaction is finished, and performing column chromatography by using a mixture of petroleum ether and ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5:1, and then obtaining a pure product with the yield of 88% and the purity of 98%.
After nuclear magnetic analysis: 1H NMR (400MHz, DMSO) δ 8.64(s,1H),7.50(d, J ═ 6.8Hz,2H),7.41-7.29(m,5H),7.27-7.15(m,7H),2.30(s,3H).13C NMR (100MHz, DMSO) δ 170.3,158.1,138.4,137.6,130.7,129.4,129.2,129.1,128.9,128.6,128.4,128.3,126.8,126.7,125.8,105.6, 20.9.
Example three: the 4-hydroxy butenolide is synthesized by the reaction of p-fluorobenzoyl formic acid and tolane, and the molecular formula is as follows:
the synthesis reaction comprises the following specific steps:
adding 0.3mmol of p-fluorobenzoylformic acid, 0.6mmol of tolane, 0.09mmol of boron trifluoride diethyl etherate and 2mL of fluorobenzene into a reaction tube in sequence, reacting for 4 hours at 70 ℃, decompressing and steaming to remove a solvent after the reaction is finished, and performing column chromatography by using a mixture of petroleum ether and ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5:1, and then obtaining a pure product with the yield of 94% and the purity of 98.5%.
After nuclear magnetic analysis: 1H NMR (400MHz, DMSO) δ 8.64(s,1H),7.52-7.46(m,2H),7.46-7.40(m,2H),7.38-7.33(m,3H),7.31-7.21(m,5H),7.20-7.13(m,2H), 13C NMR (100MHz, DMSO) δ 170.1,162.2(d, JC-F246.7 Hz),158.7,137.3,131.6(d, JC-F8.5 Hz),130.4,129.6,128.9,128.6,128.4,128.4,126.1(d, JC-F3.3 Hz),125.9,125.9,115.6(d, JC-F21.7 Hz),105.7.19F NMR (376MHz, DMSO) δ -112.0.
Example four: the 4-hydroxy butenolide is synthesized by the reaction of p-bromobenzoyl formic acid and tolane, and the molecular formula is as follows:
the synthesis reaction comprises the following specific steps:
adding 0.3mmol of p-bromobenzoyl formic acid, 0.6mmol of tolane, 0.09mmol of boron trifluoride diethyl etherate and 2mL of fluorobenzene into a reaction tube in sequence, reacting for 5h at 70 ℃, decompressing and evaporating to remove a solvent after the reaction is finished, and then carrying out column chromatography by using a mixture of petroleum ether and ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5:1, and then obtaining a pure product with the yield of 90% and the purity of 98%.
After nuclear magnetic analysis: 1H NMR (400MHz, DMSO) δ 8.71(s,1H),7.61(d, J ═ 8.4Hz,2H),7.52(d, J ═ 6.4Hz,2H),7.39-7.31(m,5H),7.28-7.18(m,5H), 13C NMR (100MHz, DMSO) δ 169.8,159.1,137.2,131.6,131.5,130.3,129.7,129.1,129.0,128.6,128.5,128.4,125.9,125.9,122.4,105.8.
Example five: the 4-hydroxy butenolide is synthesized by the reaction of p-chlorobenzoyl formic acid and tolane, and the molecular formula is as follows:
the synthesis reaction comprises the following specific steps:
adding 0.3mmol of p-chlorobenzoyl formic acid, 0.6mmol of tolane, 0.09mmol of boron trifluoride diethyl etherate and 2mL of fluorobenzene into a reaction tube in sequence, reacting for 4 hours at 70 ℃, decompressing and steaming to remove a solvent after the reaction is finished, and performing column chromatography by using a mixture of petroleum ether and ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5:1, and then obtaining a pure product with the yield of 90% and the purity of 98%.
After nuclear magnetic analysis: 1H NMR (400MHz, DMSO). delta.8.67 (s,1H),7.54-7.45(m,4H),7.44-7.32(m,5H),7.30-7.21(m,3H),7.18-7.15(m,2H).13C NMR (100MHz, DMSO). delta. 169.9,159.1,137.3,133.7,131.2,130.3,129.7,128.9,128.7,128.6,128.6,128.4,128.4,125.9,125.8,105.8.
Example six:
the 4-hydroxy butenolide is synthesized by the reaction of benzoylformic acid and di (4-methylphenyl) acetylene, and the molecular formula of the 4-hydroxy butenolide is as follows:
the synthesis reaction comprises the following specific steps:
adding 0.3mmol of benzoylformic acid, 0.6mmol of di (4-methylphenyl) acetylene, 0.09mmol of boron trifluoride diethyl etherate and 2mL of fluorobenzene into a reaction tube in sequence, reacting at 70 ℃ for 2h, evaporating the solvent under reduced pressure after the reaction is finished, and performing column chromatography by using a mixture of petroleum ether and ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5:1, thus obtaining a pure product with the yield of 85% and the purity of 98%.
After nuclear magnetic analysis: 1H NMR (400MHz, CDCl3) δ 7.42-7.34(m,4H),7.29-7.24(m,3H),7.14-7.05(m,4H),6.95(d, J ═ 8.0Hz,2H),4.87(s,1H),2.30(s,3H),2.24 (s,3H).13C NMR (100MHz, CDCl3) δ 170.9,158.7,139.5,138.7,133.6,129.2,129.1,128.7,128.6,128.6,128.3,127.9,127.0,126.2,125.5,105.4,20.9, 20.7.
Example seven: the 4-hydroxy butenolide is synthesized by the reaction of benzoylformic acid and bis (4-fluorophenyl) acetylene, and the molecular formula is as follows:
the synthesis reaction comprises the following specific steps:
adding 0.3mmol of benzoylformic acid, 0.6mmol of bis (4-fluorophenyl) acetylene, 0.09mmol of boron trifluoride diethyl etherate and 2mL of fluorobenzene into a reaction tube in sequence, reacting at 70 ℃ for 5 hours, decompressing and evaporating a solvent after the reaction is finished, and then carrying out column chromatography by using a mixture of petroleum ether and ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5:1, and then obtaining a pure product with the yield of 91% and the purity of 98%.
After nuclear magnetic analysis: 1H NMR (400MHz, DMSO) δ 8.78(s,1H),7.59-7.54(m,2H),7.46-7.37(m,5H),7.30-7.23(m,2H),7.22-7.15(m,2H),7.14-7.05(m,2H), 13C NMR (100MHz, DMSO) δ 169.9,163.6(d, JC-F ═ 18.6Hz),161.1(d, JC-F ═ 15.9Hz),157.2,133.7(d, JC-F ═ 2.9Hz),131.0(d, JC-F ═ 8.6Hz),129.6,129.3,128.9,128.5,128.3(d, JC-F ═ 8.6Hz),127.1,126.8(d, JC-F ═ 3.3Hz),115.6(d, JC-F ═ 21.8Hz),115.3(d, JC-F ═ 8.82 Hz), JC-F ═ 112.7, 110.7.7, 7.7.7H), 7.112 δ ═ 7.7 (m,2H), 13C NMR (d, JC-F ═ 2.9 Hz).
Claims (3)
1. A method for preparing 4-hydroxybutenolide from a keto acid and an alkyne, wherein the molecular formula of the 4-hydroxybutenolide is as follows:
wherein: r1 is aryl or alkyl, R2 is aryl or alkyl, R3 is aryl;
the preparation method is characterized by comprising the following steps:
step 1) adding ketonic acid, alkyne and boron trifluoride diethyl etherate into reaction equipment, taking fluorobenzene as a solvent, and reacting for a period of time at 70 ℃ to obtain a crude product and the solvent, wherein the ketonic acid is any one of benzoylformic acid, p-methylbenzoylformic acid, p-bromobenzoylformic acid, p-chlorobenzoylformic acid or p-fluorobenzoylformic acid;
step 2) carrying out decompression operation on the product obtained in the step 1 to evaporate the solvent;
and 3) carrying out column chromatography on the product obtained in the step 2 by using an organic solvent to obtain the 4-hydroxy butenolide.
2. The method of claim 1 for preparing 4-hydroxybutenolide with a keto acid and an alkyne, comprising: the alkyne is any one of tolane, di (4-methylphenyl) acetylene or di (4-fluorophenyl) acetylene.
3. The method of claim 1 for preparing 4-hydroxybutenolide with a keto acid and an alkyne, comprising: the molar ratio of the keto acid, the alkyne, and the boron trifluoride etherate is 1: 2: 0.3.
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-
2015
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| CN103420959A (en) * | 2012-05-24 | 2013-12-04 | 北京服装学院 | Synthetic method of hydroxyl butenolide and congener thereof |
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|---|
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