CN106349071B - The method that no catalyst and condensing agent prepare fatty acid trifluoro ethyl ester - Google Patents

The method that no catalyst and condensing agent prepare fatty acid trifluoro ethyl ester Download PDF

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CN106349071B
CN106349071B CN201610740931.4A CN201610740931A CN106349071B CN 106349071 B CN106349071 B CN 106349071B CN 201610740931 A CN201610740931 A CN 201610740931A CN 106349071 B CN106349071 B CN 106349071B
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fatty acid
ethyl ester
acid
trifluoro ethyl
trifluoroethyl
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CN106349071A (en
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张成潘
韩秋燕
杨静
赵成龙
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Wuhan University of Technology WUT
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

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Abstract

The invention discloses a kind of methods that no catalyst and condensing agent prepare fatty acid trifluoro ethyl ester, comprising the following steps: mixes fatty acid with alkali, trifluoroethyl aryl trivalent iodine reagent is added and is stirred to react 1~72h at -20 DEG C to 100 DEG C and obtains reaction product.The molar ratio of fatty acid and trifluoroethyl aryl trivalent iodine reagent is 1:(0.2~5)；The molar ratio of fatty acid and alkali is 1:(0.2~5).The present invention does not need addition catalyst and condensing agent, it might even be possible to not need organic solvent；And trifluoroethyl reagent PhICH used2CF3] [X] can be by CF3H2I facilitates synthesis；Raw materials used to be easy to get, reaction condition is mild, and functional group compatibility is good, and wide application range of substrates is easy to operate, and almost can obtain target product with quantitative yield.

Description

The method that no catalyst and condensing agent prepare fatty acid trifluoro ethyl ester
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of no catalyst and condensing agent prepare fatty acid trifluoro The method of ethyl ester.
Background technique
Aliphatic ester due to that can be biodegradable, it is most it is nontoxic it is non-stimulated, partially there is the oxidation resistant property of antibacterial, because This is widely used in the industries such as food, beauty, pharmacy, processing.In recent years, with the development of organic fluorine chemistry, fatty acid three Fluoro ethyl ester (RCO2CH2CF3) application be also concerned.The fatty acid trifluoro for medicine and Material Field being currently known Ethyl ester, mainly unsaturated fatty acid trifluoro ethyl ester are mainly used to synthetic anionic exchange membrane, drug delivery medium, modification Material surface etc. (a) A.Arafat, M.Giesbers, M.Rosso, E.J.R.K.R.G.White, L.Yang,M.R.Linford,H.Zuilhof,Langmuir 2007,23,6233-6244；b)W.Du,Z.Xu,A.M.K.Zhang,J.R.Leonard,K.L.Wooley,Bioconjugate Chem.2008,19,2492-2498；c) W.Biesta,B.van Lagen,V.S.Gevaert,A.T.M.Marcelis,J.M.J.Paulusse,M.W.F.Nielen, H.Zuilhof,Chem.Mater.2012,24,4311-4318).There are also short chain fatty acids trifluoro ethyl esters to be used as lithium ion Electrolyte material (J.G.Petrov, E.E.Polymeropoulos, the H. of batteryLangmuir2007,23, 2623-2630).Simultaneously because trifluoroethyl (CH2CF3) special structure and electronic effect, long chain fatty acids trifluoro ethyl ester single layer Molecular film gas-water interface show with the antipodal surface potential of not fluorine-containing aliphatic ester and dipole moment etc. (W.Lu, K.Xie,Z.Chen,Y.Pan,C.M.Zheng,J.Fluorine Chem.2014,161,110-119).In view of fatty acid trifluoro The importance and serviceability of ethyl ester develop the method being simple and efficient and synthesize such compound, is of great significance.But at present The synthetic method for the fatty acid trifluoro ethyl ester known generally uses fatty acid directly to react preparation with trifluoroethanol.But due to trifluoro The nucleophilicity of ethyl alcohol is weaker, and reaction usually needs condensing agent and catalyst to participate in, simultaneous reactions condition harshness, functional group tolerance Difference, low yield.It is related to the synthesis of long chain fatty acids, particularly the long chain fatty acids trifluoro ethyl ester containing susceptible functionality, it is even more fresh It has been reported that.
Summary of the invention
It does not need to add any catalyst and condensing agent preparation long chain fatty acids trifluoro it is an object of that present invention to provide one kind The method of ethyl ester, compared with other synthetic methods, this method raw material is easy to get, and reaction condition is mild, and functional group compatibility is good, substrate It is applied widely, it is easy to operate, and target product can be obtained with quantitative yield.
In order to achieve the above objectives, as follows using technical solution:
The method for preparing fatty acid trifluoro ethyl ester, comprising the following steps:
Fatty acid is mixed with alkali, trifluoroethyl aryl trivalent iodine reagent is added and is stirred to react at -20 DEG C to 100 DEG C 1~72h obtains reaction product.
According to the above scheme, fatty acid mixes in organic solvent with alkali, adds trifluoroethyl aryl trivalent iodine reagent.
According to the above scheme, the organic solvent be acetonitrile, toluene, ortho-xylene, methylene chloride, dimethyl sulfoxide, DMF, Any one of THF, 1,4- dioxane, chloroform, benzene, 1,2- dichloroethanes, ethyl acetate, n-hexane, hexamethylene.
It according to the above scheme, further include that reaction product is added to methylene chloride extraction, dichloromethane solution decompression rotation after separation Dry, residue obtains target product through column chromatographic purifying.
According to the above scheme, the molar ratio of fatty acid and trifluoroethyl aryl trivalent iodine reagent is 1:(0.2~5)；Fatty acid Molar ratio with alkali is 1:(0.2~5).
According to the above scheme, the fatty acid is long chain fatty acids, and structural formula is expressed as RCOOH；Wherein R is containing 5-29 carbon Alkyl, aralkyl, heterocycle, simultaneously ring or the condensed ring of atom.
According to the above scheme, optimally, the fatty acid be lauric acid, myristic acid, palmitic acid, behenic acid, oleic acid, Linolenic acid, adamantane acetic acid or oleanolic acid etc..
According to the above scheme, the structural formula of the trifluoroethyl aryl trivalent iodine reagent is [ArICH2CF3] [X], wherein Ar is Phenyl ring, substituted benzene ring, heteroaromatic or derivatives thereof；X is-OTf、-BF4、-PF6、-SbF6Or-N(SO2CF3)2。
According to the above scheme, the alkali is inorganic base or organic base；Inorganic base includes LiHCO3, NaHCO3, KHCO3, Li2CO3, Na2CO3, K2CO3, Cs2CO3, K3PO4, K2HPO4, KH2PO4, LiOH, NaOH, KOH, NaH, KH, CaH2, NaOCH3, NaOCH2CH3；Organic base includes HN (CH2CH3)2, N (CH2CH3)3, HN (CH (CH3)2)2, N (C4H9)3, DABCO, DBU, pyridine.
According to the above scheme, optimally, the molar ratio of fatty acid and trifluoroethyl aryl trivalent iodine reagent is 1:1.5；Fat The molar ratio of acid and alkali is 1:1；Reaction time is for 24 hours that reaction temperature is between 20~30 DEG C.
According to the above scheme, optimally, alkali K2CO3、Cs2CO3Or K3PO4。
This method prepares reaction used in fatty acid trifluoro ethyl ester, and representative equation is as follows:
Compared with the existing technology, the beneficial effects of the present invention are: the present invention not to need addition catalyst and condensing agent, very Organic solvent can extremely not needed；And trifluoroethyl reagent PhICH used2CF3] [X] can be by CF3H2I facilitates synthesis. The raw materials used in the present invention is easy to get, and reaction condition is mild, and functional group compatibility is good, and wide application range of substrates is easy to operate, and almost Target product can be obtained with quantitative yield.
Specific embodiment
With reference to embodiment, the invention will be further described, but not as to the scope of the present invention Limitation.
The long chain fatty acids trifluoro ethyl ester that the present invention synthesizes, typical structure is as follows, but protects not as to the present invention Protect the limitation of range.
By taking the preparation of trifluoromethanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine as an example: by trifluoroacetic anhydride, trifluoroacetic acid, peroxide Change hydrogen and trifluoro iodoethane mixture, be stirred to react 20h at normal temperature, prepares CF3CH2I(OCOCF3)2, then CF3CH2I (OCOCF3)2It is reacted for 24 hours under the conditions of 0 DEG C with benzene and trifluoromethanesulfonic acid, trifluoromethanesulfonic acid trifluoroethyl phenyl trivalent can be prepared Salt compounded of iodine.
Embodiment 1
Lauric acid (60.1mg, 0.30mmol) and potassium carbonate (41.5mg, 0.30mmol) is mixed, trifluoromethanesulfonic acid is added The dichloromethane solution (3mL) of trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol), is stirred to react 6h at room temperature. Reaction is finished, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, and residue is through (the elution of column chromatographic purifying Agent is petroleum ether) to get lauric acid trifluoro ethyl ester (95%yield).1H NMR(500MHz,CDCl3) δ 4.46 (q, J= 10.0Hz, 2H), 2.40 (t, J=5Hz, 2H), 1.28 (d, J=20Hz, 1H), 0.88 (t, J=5.0Hz, 3H)19F NMR (471MHz,CDCl3)δ-73.9(t,3F).13C NMR(126MHz,CDCl3) δ 172.2,123.0 (q, J=277.2Hz), 60.1 (q, J=36.5Hz), 33.7,31.9,29.6,29.6,29.4,29.3,29.2,29.0,24.7,22.7,14.1.
Embodiment 2
Myristic acid (68.5mg, 0.30mmol) and tripotassium phosphate (63.7mg, 0.30mmol) is mixed, trifluoro is added The toluene solution (3mL) of methanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol), is stirred to react in 100 DEG C 1h, reaction are finished, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, and residue (is washed through column chromatographic purifying De- agent is petroleum ether), product section is collected, oil well pump is concentrated up to myristic acid trifluoro ethyl ester (93%yield).1H NMR (500MHz,CDCl3) δ 4.46 (q, J=8.0Hz, 2H), 2.40 (t, J=2Hz, 2H), 1.28 (d, J=20Hz, 1H), 0.88 (t, J=5.0Hz, 3H)19F NMR(471MHz,CDCl3)δ-73.9(t,3F).13C NMR(126MHz,CDCl3)δ172.2, 123.0 (q, J=277.2Hz), 60.1 (q, J=36.5Hz), 33.7,31.9,29.7,29.6,29.6,29.4,29.4, 29.2,29.0,24.7,22.7,14.1.
Embodiment 3
Palmitic acid (76.9mg, 0.30mmol) and cesium carbonate (97.7mg, 0.30mmol) is uniformly mixed, trifluoro is added Isosorbide-5-Nitrae-dioxane solution (3mL) of methanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol), is stirred in 60 DEG C Mix reaction for 24 hours, reaction is finished, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, and residue is chromatographed through column It purifies (eluant, eluent is petroleum ether) and collects product section, oil well pump is concentrated up to hexadecanoic acid trifluoro ethyl ester (99%yield).1H NMR(400MHz,CDCl3) δ 4.46 (q, J=8.0Hz, 2H), 2.41 (t, J=8Hz, 2H), 1.25 (s, 26H), 0.88 (t, J =6.0Hz, 3H)19F NMR(376MHz,CDCl3)δ-73.9(t,3F).13C NMR(126MHz,CDCl3)δ172.2,123.0 (q, J=277.2Hz), 60.1 (q, J=36.5Hz), 33.7,31.9,29.7,29.7,29.6,29.4,29.4,29.2, 29.0,24.7,22.7,14.1.
Embodiment 4
After mixing by palmitic acid (76.9mg, 0.30mmol) and cesium carbonate (97.7mg, 0.30mmol), trifluoro is added Methanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol), is not added any solvent, is stirred to react at room temperature 48h, reaction are finished, and crude product collects product section through column chromatographic purifying (eluant, eluent is petroleum ether), and oil well pump is concentrated up to hexadecanoic acid Trifluoro ethyl ester (98%yield).1H NMR(400MHz,CDCl3) δ 4.46 (q, J=8.0Hz, 2H), 2.41 (t, J=8Hz, 2H), 1.25 (s, 26H), 0.88 (t, J=6.0Hz, 3H)19F NMR(376MHz,CDCl3)δ-73.9(t,3F).13C NMR (126MHz,CDCl3) δ 172.2,123.0 (q, J=277.2Hz), 60.1 (q, J=36.5Hz), 33.7,31.9,29.7, 29.7,29.6,29.4,29.4,29.2,29.0,24.7,22.7,14.1.
Embodiment 5
Behenic acid (102.2mg, 0.30mmol) and potassium hydroxide (16.8mg, 0.30mmol) is uniformly mixed, then The dichloromethane solution (3mL) of trifluoromethanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol) is added, in room 72h is stirred to react under temperature, reaction is finished, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, residue warp Column chromatographic purifying (eluant, eluent is petroleum ether) collects product section, and oil well pump is concentrated up to behenic acid trifluoro ethyl ester (78% yield)。1H NMR(500MHz,CDCl3) δ 4.46 (q, J=10Hz, 2H), 2.41 (t, J=5Hz, 2H), 1.28 (d, J= 20.0Hz, 38H), 0.88 (t, J=6.0Hz, 3H)19F NMR(471MHz,CDCl3)δ-73.9(t,3F).13C NMR (126MHz,CDCl3) δ 172.2,123.0 (q, J=277.2Hz), 60.1 (q, J=32.8Hz), 33.7,31.9,29.7, 29.6,29.6,29.4,29.4,29.2,29.0,24.7,22.7,14.1.
Embodiment 6
Oleic acid (84.7mg, 0.30mmol) and cesium carbonate (97.7mg, 0.30mmol) is uniformly mixed, fluoroform is added The dichloromethane solution (3mL) of sulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol), stirring is anti-at room temperature 32h is answered, reaction is finished, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, and residue is through column chromatographic purifying (eluant, eluent is petroleum ether) collects product section, and oil well pump is concentrated up to oleic acid trifluoro ethyl ester (90%yield).1H NMR (500MHz,CDCl3) δ 5.34 (t, J=15.0Hz, 2H), δ 4.46 (q, J=7.5Hz, 2H), 2.41 (t, J=8Hz, 2H), 2.01 (t, 3H), 0.88 (t, J=6.0Hz, 3H)19F NMR(471MHz,CDCl3)δ-73.9(t,3F).13C NMR (126MHz,CDCl3) δ 172.1,130.1,129.7,123.0 (q, J=277.2Hz), 60.1 (q, J=36.5Hz), 33.6, 31.9,29.8,29.7,29.5,29.3,29.1,29.0,28.9,27.2,27.1,24.7,22.7,14.1.
Embodiment 7
After mixing by linolenic acid (83.5mg, 0.30mmol) and cesium carbonate (97.7mg, 0.30mmol), trifluoro is added The dichloromethane solution (3mL) of methanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol), is stirred at room temperature 12h is reacted, reaction is finished, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, and residue chromatographs pure through column Change (eluant, eluent is petroleum ether), collect product section, oil well pump is concentrated up to linolenic acid trifluoro ethyl ester (76%yield).1H NMR (500MHz,CDCl3) δ) δ 5.37 (s, 6H), δ 4.46 (q, J=7.5Hz, 2H), δ 2.81 (s, 4H), δ 2.01 (t, 3H), δ 2.41 (t, J=5.0Hz, 2H), δ 2.07 (q, J=5.0Hz, 4H), δ 1.29 (d, J=30.0Hz, 10H), δ 0.98 (t, J= 5.0Hz,3H).19F NMR(471MHz,CDCl3)δ-73.9(t,3F).13C NMR(126Hz,CDCl3)δ172.1,132.0, (130.2,128.3,128.2,127.8,127.1,123.0 q, J=277.2Hz), 60.1 (q, J=36.5Hz), 33.6, 29.7,29.5,29.1,29.0,28.9,27.2,25.6,25.5,24.7,20.6,14.3.
Embodiment 8
After mixing by adamantane acetic acid (58.3mg, 0.30mmol) and cesium carbonate (97.7mg, 0.30mmol), it is added The dichloromethane solution (3mL) of trifluoromethanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol) is stirred in 0 DEG C For 24 hours, reaction is finished for reaction, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, and residue chromatographs pure through column Change (eluant, eluent is petroleum ether), collect product section, oil well pump is concentrated up to adamantane trifluoro ethyl ester (92%yield).1H NMR (500MHz,CDCl3) δ 4.45 (q, J=5.0Hz, 2H), 2.17 (s, 2H), 1.98 (s, 3H), 1.62 (t, J=10.0Hz, 12H).19F NMR(471MHz,CDCl3)δ-73.6(t,3F).13C NMR(100MHz,CDCl3) δ 170.0,123.0 (q, J= 220.0Hz), 60.0 (q, J=37.0Hz), 48.2,42.2,36.6,32.9,28.6.
Embodiment 9
By oleanolic acid (137.0mg, 0.30mmol) and cesium carbonate (97.7mg, 0.30mmol), after mixing, it is added The dichloromethane solution (3mL) of trifluoromethanesulfonic acid trifluoroethyl phenyl trivalent salt compounded of iodine (196.3mg, 0.45mmol), extremely in -20 DEG C It is stirred to react at room temperature for 24 hours, reaction is finished, and methylene chloride extraction (3 × 3mL) is added.Dichloromethane solution decompression is spin-dried for, residue Through column chromatographic purifying (eluant, eluent is petroleum ether: ethyl acetate=5:1), product section is collected, oil well pump is concentrated up to oleanolic acid Trifluoro ethyl ester (94%yield).1H NMR(400MHz,CDCl3) δ 5.31 (dd, J=4.0,4.0Hz, 1H), δ 4.45 (q, J= 4.0Hz, 2H), 3.21 (dd, J=12.0,4.0Hz, 1H), 2.86 (dd, J=12.0,4.0Hz, 1H), 2.01 (ddd, J= 12.0,12.0,4.0Hz,1H),1.89(m,1H)1.63(m,14H),1.42(m,3H),1.19(m,1H),1.14(s,3H), 0.98(s,3H),0.96(m,1H),0.92(s,3H),0.90(s,6H),0.78(s,3H),0.71(s,3H).19F NMR (376MHz,CDCl3)δ-73.6(t,3F).

Claims (9)

1. the method for preparing fatty acid trifluoro ethyl ester, it is characterised in that the following steps are included:
Fatty acid is mixed with alkali, trifluoroethyl aryl trivalent iodine reagent is added, at -20 DEG C to 100 DEG C, it is stirred to react 1~ 72h obtains reaction product.
2. the method for preparing fatty acid trifluoro ethyl ester as described in claim 1, it is characterised in that fatty acid is blended in organic with alkali In solvent, trifluoroethyl aryl trivalent iodine reagent is added；The organic solvent is acetonitrile, toluene, ortho-xylene, dichloromethane Alkane, dimethyl sulfoxide, DMF, THF, 1,4- dioxane, chloroform, benzene, 1,2- dichloroethanes, ethyl acetate, n-hexane, hexamethylene Any one.
3. the method for preparing fatty acid trifluoro ethyl ester as described in claim 1, it is characterised in that further include that reaction product is added Methylene chloride extraction, dichloromethane solution decompression is spin-dried for after separation, and residue obtains target product through column chromatographic purifying.
4. the method for preparing fatty acid trifluoro ethyl ester as described in claim 1, it is characterised in that fatty acid and trifluoroethyl aryl The molar ratio of trivalent iodine reagent is 1:(0.2~5)；The molar ratio of fatty acid and alkali is 1:(0.2~5).
5. the method for preparing fatty acid trifluoro ethyl ester as described in claim 1, it is characterised in that the fatty acid is carbon atom number For the fatty acid of 6-30.
6. as claimed in claim 5 prepare fatty acid trifluoro ethyl ester method, it is characterised in that the fatty acid include lauric acid, Any one of myristic acid, palmitic acid, behenic acid, oleic acid, linolenic acid, adamantane acetic acid, oleanolic acid.
7. the method for preparing fatty acid trifluoro ethyl ester as described in claim 1, it is characterised in that the trifluoroethyl aryl trivalent The structural formula of iodine reagent is [ArICH2CF3] [X], wherein Ar is phenyl ring, substituted benzene ring or derivatives thereof；X is-OTf ,-BF4、- PF6、-SbF6Or-N (Tf)2。
8. the method for preparing fatty acid trifluoro ethyl ester as described in claim 1, it is characterised in that the alkali is inorganic base or organic Alkali；The inorganic base is LiHCO3, NaHCO3, KHCO3, Li2CO3, Na2CO3, K2CO3, Cs2CO3, K3PO4, K2HPO4, KH2PO4, LiOH, NaOH, KOH, NaH, KH, CaH2, NaOCH3, NaOCH2CH3In any one；Organic base is HN (CH2CH3)2, N (CH2CH3)3, HN (CH (CH3)2)2, N (C4H9)3, DABCO, DBU, any one in pyridine.
9. the method for preparing fatty acid trifluoro ethyl ester as described in claim 1, it is characterised in that fatty acid and trifluoroethyl aryl The molar ratio of trivalent iodine reagent is 1:1.5；The molar ratio of fatty acid and alkali is 1:1；Reaction time is for 24 hours that reaction temperature is 20 Between~30 DEG C.
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