CN110981720A - Diaryl acetate compound and preparation method thereof - Google Patents
Diaryl acetate compound and preparation method thereof Download PDFInfo
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Abstract
The invention provides a diaryl acetate compound and a preparation method thereof, and the preparation method comprises the following steps: (1) adding diaryl 1, 2-diketone compounds, alcohol compounds, trialkyl phosphite and a photocatalyst into a reaction vessel, and adding a solvent for dissolving to obtain a reaction solution; (2) irradiating the reaction solution by using a light source and stirring the reaction solution until the reaction is complete; (3) and after the reaction is finished, recovering the solvent under reduced pressure and purifying by column chromatography to obtain the diaryl acetate compound. The invention starts from easily obtained diaryl 1, 2-diketone, has mild and green reaction conditions, does not need precious transition metal catalysis, is economic and environment-friendly, and has higher practicability.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to diaryl acetate compounds and a preparation method thereof.
Background
Diaryl acetate structures are widespread among natural products and are available for many pharmaceutical molecules such as swertin and dinitrogen. Research shows that the structure has antiviral, rheumatism eliminating, antitumor, central nervous activity and serotonin dopamine reuptake inhibiting activity. The related documents are: (a) Xu, H.; Lv, M.; Tian, X. Curr. Med. chem.2009, 16, 327, (b) Keller, H.; Schafner, R.; Carruba, M. O.; Burkard, W.P.; Pieri, M.; Bonetti, E. P.; Scherschlich, R.; Prada, M. D.; Haefely, W.E. adv. biochem. Psychopharmacol. 1982, 31, 249. (c) Jacob, J. N.; Nichols, D. E.; Kohli, J. D.; Glock, D.J. chem. 1981, 24, 1013.
The preparation of diaryl acetic acid is mainly a transition metal catalyzed coupling method starting from monoaryl acetic acid ester. The recently developed metal coupling method of 2-azido acetate overcomes the harsh conditions of high temperature, strong alkali and the like of the traditional method.
Related preparation and activity patents are also: (1) in the Chinese patent application of Zjunliang, university of east China, "a method for selective C-H bond functionalization of phenol and aniline under the catalysis of gold" (CN 103936537A), a method for realizing coupling of phenol or aniline and azido acetate by utilizing a gold catalyst is disclosed, and synthesis of diaryl acetate is realized; (2) international patent publication WO2007033781A1 discloses a palladium catalyzed coupling reaction between an aryl acetate and an aryl bromide directly under strongly basic conditions; (3) leehen in International patent WO2002079339A2 discloses the coupling of 2-bromoacetate and arylboronic acid under Pd (0) catalysis to form diarylacetate; (4) zhejiang Hebei pesticide chemical Co Ltd discloses a synthesis method for synthesizing diaryl acetate-bromopropylate by using glyoxylic acid, bromobenzene and isopropanol in Chinese patent 'a synthesis method of bromopropylate' (CN 103936537A).
However, the above preparation methods all use severe conditions such as strong alkali, and the reaction is not economical because the catalyst is catalyzed by expensive transition metal.
Disclosure of Invention
The invention provides a diaryl acetate compound and a preparation method thereof, which solve the problems of harsh reaction conditions and low efficiency in the prior art.
The technical scheme for realizing the invention is as follows:
a preparation method of diaryl acetate compounds comprises the following steps:
(1) adding diaryl 1, 2-diketone compounds, alcohol compounds, trialkyl phosphite and a photocatalyst into a reaction vessel, and adding a solvent for dissolving to obtain a reaction solution;
(2) irradiating the reaction solution by using a light source and stirring the reaction solution until the reaction is complete;
(3) and after the reaction is finished, recovering the solvent under reduced pressure and purifying by column chromatography to obtain the diaryl acetate compound.
The structural formula of the diaryl 1, 2-diketone compound in the step (1) is as follows:
wherein Ar is1And Ar2The same or different, and is selected from any one of phenyl, substituted phenyl, aromatic heterocycle, condensed ring aryl and condensed aromatic heterocycle substituent.
The structural formula of the alcohols in the step (1) is ROH, wherein R is a linear chain or branched chain alkyl of C1-C20.
The photocatalyst in the step (1) is DPZ, and the specific synthesis steps can be referred to as ZHao, Y., Zhang, C., Chin, K, F., Pyrela, O., Wei, G., Liu, H., Bure š, F., Jiang, Z.RSC A,dv.2014.4(57), 30062. The structural formula of the photocatalyst is as follows:
。
the structural formula of the trialkyl phosphite in the step (1) is as follows: p (OR')3Wherein R' is a linear or branched alkyl of C1-C10.
The solvent in the step (1) is any one of acetonitrile, propionitrile, isopropyl nitrile, n-butyl nitrile, isobutyl nitrile, tert-butyl nitrile, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, ethylbenzene, p-xylene, diethyl ether, THF, dioxane and dimethoxyethane.
In the step (1), the molar ratio of diaryl 1, 2-diketone compound, alcohol compound, trialkyl phosphite and photocatalyst is 1 (1-10): (1-3): (0.001-0.1), and the concentration of diaryl 1, 2-dione compound in the reaction solution is 0.01-1.0M.
The light source in the step (2) is a CFL bulb, sunlight or an LED lamp, the power range of the CFL bulb is 9-100W, the wavelength range of the LED lamp is 445-455nm, and the power is 1-10W.
The reaction process in the step (2) is protected by argon or nitrogen, and the reaction time is 2-7 days
The structural formula of the prepared diaryl acetate compound is as follows:
The reaction formula is as follows:
wherein Ar is1And Ar2The same or different, is selected from phenyl, substituted phenyl, aromatic heterocycle, condensed ring aryl and condensed aromatic heterocycle substituent; r is a straight chain or branched chain alkyl of C1-C20; r' is a straight chain or branched chain alkyl of C1-C10.
The invention has the beneficial effects that: the invention starts from easily obtained diaryl 1, 2-diketone, has mild and green reaction conditions, does not need precious transition metal catalysis, is economic and environment-friendly, and has higher practicability.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, 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 obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
Preparation of ethyl 2, 2-diphenylacetate (2 a):
the specific synthesis steps and the characterization are as follows:
benzil 1a (21 mg, 0.1 mmol, 1.0 equiv.) and P (OEt) were combined in a 10 ml Schlenk tube3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, the reaction was stirred for 48 hours under 3W LED (450 nm) irradiation at room temperature, and the reaction was completed by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same applies hereinafter, PE: EA = 20: 1) to give the diaryl acetate compound 2a, 21.5 mg, 90%.
1H NMR (300 MHz, Chloroform-d) δ 7.41 – 7.23 (m, 10H), 5.04 (s, 1H),4.24 (q,J= 7.1 Hz, 2H), 1.28 (t,J= 7.1 Hz, 3H)。
13C NMR (75 MHz, CDCl3) δ 172.44, 138.80, 128.59, 128.54, 127.18,61.15, 57.16, 14.12; HRMS (ESI) m/z 241.1226 (M+H+), calc. for C6H17O2241.1223。
Using the procedure of example 1, varying the reaction conditions, the results are shown in the following table:
example 2
Preparation of ethyl 2, 2-bis (4-butylphenyl) acetate (2 b):
the specific synthesis steps and the characterization are as follows:
benzil compound 1b (32.2 mg, 0.1 mmol, 1.0 equiv.) and P (OEt) were combined in a 10 ml Schlenk tube3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, the reaction was stirred for 48 hours under 3W LED (450 nm) irradiation at room temperature, and the reaction was completed by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same applies hereinafter, PE: EA = 20: 1) to give a diaryl acetate compound 2b, 27 mg, 77%.
1H NMR (300 MHz, Chloroform-d) δ 7.14 (d,J= 7.9 Hz, 4H), 7.04 (d,J= 8.0 Hz, 4H), 4.86 (s, 1H), 4.11 (q,J= 7.1 Hz, 2H), 2.49 (t,J= 7.7 Hz,4H), 1.55 – 1.43 (m, 4H), 1.33 – 1.22 (m, 4H), 1.17 (t,J= 7.1 Hz, 3H), 0.83(t,J= 7.3 Hz, 6H)。
13C NMR (75 MHz, CDCl3) δ 172.9, 141.7, 136.2, 128.7, 128.6, 128.4,128.4, 61.1, 56.5, 35.3, 33.5, 22.4, 14.2, 14.0；HRMS (ESI) m/z 353.2480 (M+H+), calc. for C24H33O2353.2475。
Example 3
Preparation of ethyl 2, 2-bis (4-chlorophenyl) acetate (2 c):
the specific synthesis steps and the characterization are as follows:
benzil compound 1c (27.9 mg, 0.1 mmol, 1.0 equiv.) and P (OEt) were combined in a 10 ml Schlenk tube3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, the reaction was stirred for 48 hours under 3W LED (450 nm) irradiation at room temperature, and the reaction was completed by TLC. The reaction mixture was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same applies hereinafter, PE: EA = 20: 1) to give a diarylacetate compound 2c, 22 mg, 71%。
1H NMR (300 MHz, Chloroform-d) δ 7.30 (d,J= 8.6 Hz, 4H), 7.22 (d,J= 8.6 Hz, 4H), 4.94 (s, 1H), 4.21 (q,J= 7.1 Hz, 2H), 1.26 (t,J= 7.1 Hz,3H)。
13C NMR (75 MHz, CDCl3) δ 171.8, 136.8, 133.4, 129.9, 128.8, 61.5,55.8, 14.1；HRMS (ESI) m/z 309.0445 (M+H+), calc. for C16H15Cl2O2309.0444。
Example 4
Preparation of ethyl 2, 2-bis (4-fluorophenyl) acetate (2 d):
the specific synthesis steps and the characterization are as follows:
benzil compound 1d (24.6 mg, 0.1 mmol, 1.0 equiv.) and P (OEt) were combined in a 10 ml Schlenk tube3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, the reaction was stirred for 48 hours under 3W LED (450 nm) irradiation at room temperature, and the reaction was completed by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same applies hereinafter, PE: EA = 20: 1) to give a diaryl acetate compound 2d, 13 mg, 47%.
1H NMR (300 MHz, Chloroform-d) δ 7.26 (dd,J= 8.4, 5.6 Hz, 4H), 7.01(t,J= 8.7 Hz, 4H), 4.95 (s, 1H), 4.20 (q,J= 7.1 Hz, 2H), 1.25 (t,J= 7.2Hz, 3H)。
13C NMR (75 MHz, CDCl3) δ 172.2, 163.7, 160.4, 134.4, 134.4, 130.1,130.0, 115.7, 115.4, 77.4, 77.0, 76.6, 61.4, 55.5, 14.1；HRMS (ESI) m/z277.1033 (M+H+), calc. for C16H15F2O2277.1035。
Example 5
Preparation of ethyl 2, 2-bis (3-methoxyphenyl) acetate (2 e):
the specific synthesis steps and the characterization are as follows:
benzil compound 1e (27 mg, 0.1 mmol, 1.0 equiv.) and P (OEt) were combined in a 10 ml Schlenk tube3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, the reaction was stirred for 48 hours under 3W LED (450 nm) irradiation at room temperature, and the reaction was completed by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same shall apply hereinafter, PE: EA = 20: 1) to give the diaryl acetate compound 2e, 13 mg, 43%.
1H NMR (300 MHz, Chloroform-d) δ 7.23 (t,J= 7.8 Hz, 2H), 6.95 –6.83 (m, 4H), 6.80 (dd,J= 8.3, 2.5 Hz, 2H), 4.95 (s, 1H), 4.21 (q,J= 7.1Hz, 2H), 3.77 (s, 6H), 1.26 (t,J= 7.2 Hz, 3H)。
13C NMR (75 MHz, CDCl3) δ 172.2, 159.7, 140.0, 129.5, 121.0, 114.5,112.5, 61.2, 57.0, 55.2, 14.2；HRMS (ESI) m/z 301.1437 (M+H+), calc. forC18H21O4301.1434。
Example 6
Preparation of ethyl 2, 2-bis (2-fluorophenyl) acetate (2 f):
the specific synthesis steps and the characterization are as follows:
benzil compound 1f (24.6 mg, 0.1 mmol, 1.0 equiv.) and P (OEt) were combined in a 10 ml Schlenk tube3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, and the mixture was irradiated with a 3W LED (450 nm) at room temperature, followed by stirring and reacting for 48 hoursIn hours, the reaction was complete by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same applies hereinafter, PE: EA = 20: 1) to give a diaryl acetate compound 2f, 16 mg, 58%.
1H NMR (300 MHz, Chloroform-d) δ 7.33 – 7.14 (m, 4H), 7.14 – 6.96 (m,4H), 5.53 (s, 1H), 4.23 (q,J= 7.1 Hz, 2H), 1.24 (t,J= 7.1 Hz, 3H)。
13C NMR (75 MHz, CDCl3) δ 171.2, 162.2, 159.0, 130.0, 130.0, 129.3,129.2, 124.9, 124.7, 124.2, 124.2, 115.7, 115.4, 61.6, 43.4, 14.1；HRMS (ESI)m/z 277.1035 (M+H+), calc. for C16H15F2O2277.1035。
Example 7
Preparation of ethyl 2, 2-bis (2-chlorophenyl) acetate (2 g):
the specific synthesis steps and the characterization are as follows:
in a 10 ml Schlenk tube, 1g (27.9 mg, 0.1 mmol, 1.0 equiv.) of a benzil compound and P (OEt)3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, the reaction was stirred for 48 hours under 3W LED (450 nm) irradiation at room temperature, and the reaction was completed by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same applies hereinafter, PE: EA = 20: 1) to obtain 2g, 21.6 mg, 70% of the diarylacetate compound.
1H NMR (300 MHz, Chloroform-d) δ 7.48 – 7.35 (m, 2H), 7.23 (td,J=7.4, 6.5, 3.6 Hz, 4H), 7.13 – 7.02 (m, 2H), 5.81 (s, 1H), 4.25 (q,J= 7.1Hz, 2H), 1.26 (t,J= 7.1 Hz, 3H)。
13C NMR (75 MHz, CDCl3) δ 171.4, 135.3, 134.7, 129.8, 129.8, 128.8,126.9, 61.6, 51.7, 14.1.；HRMS (ESI) m/z 309.0446 (M+H+), calc. for C16H15Cl2O2309.0444。
Example 8
Preparation of ethyl 2, 2-bis (3-trifluoromethylphenyl) acetate (2 h):
the specific synthesis steps and the characterization are as follows:
benzil compound 1h (34.6 mg, 0.1 mmol, 1.0 equiv.) and P (OEt) in a 10 ml Schlenk tube3(33.2 mg, 0.2mmol, 2.0 equiv.) was dissolved in DCE (1.0 ml), EtOH (11.7. mu.L, 0.2mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1. mu. mol) were added, the reaction was stirred for 48 hours under 3W LED (450 nm) irradiation at room temperature, and the reaction was completed by TLC. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same applies hereinafter, PE: EA = 20: 1) to give a diaryl acetate compound 2h, 19 mg, 50%.
1H NMR (300 MHz, Chloroform-d) δ 7.48 – 7.35 (m, 2H), 7.23 (td,J=7.4, 6.5, 3.6 Hz, 4H), 7.13 – 7.02 (m, 2H), 5.81 (s, 1H), 4.25 (q,J= 7.1Hz, 2H), 1.26 (t,J= 7.1 Hz, 3H)。
13C NMR (75 MHz, CDCl3) δ 171.4, 135.3, 134.7, 129.8, 129.8, 128.8,126.9, 61.6, 51.7, 14.1.；HRMS (ESI) m/z 377.0977 (M+H+), calc. for C18H15F6O2377.0971。
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A preparation method of diaryl acetate compounds is characterized by comprising the following steps:
(1) adding diaryl 1, 2-diketone compounds, alcohol compounds, trialkyl phosphite and a photocatalyst into a reaction vessel, and adding a solvent for dissolving to obtain a reaction solution;
(2) irradiating the reaction solution by using a light source and stirring the reaction solution until the reaction is complete;
(3) and after the reaction is finished, recovering the solvent under reduced pressure and purifying by column chromatography to obtain the diaryl acetate compound.
2. The method for preparing diaryl acetate compounds according to claim 1, wherein the structural formula of the diaryl 1, 2-dione compounds in step (1) is as follows:
wherein Ar is1And Ar2The same or different, and is selected from any one of phenyl, substituted phenyl, aromatic heterocycle, condensed ring aryl and condensed aromatic heterocycle substituent.
3. The method for preparing diaryl acetate compounds according to claim 1, wherein the alcohol in step (1) has a structural formula of ROH, wherein R is a linear or branched alkyl group of C1-C20.
4. The method for preparing diaryl acetate based compound according to claim 1, wherein the photocatalyst in the step (1) has the following structural formula:
。
5. the process for producing a diaryl acetate-based compound according to claim 1, wherein: the trialkyl phosphite in the step (1) has the structural formula of P (OR')3Wherein R' is a linear or branched alkyl of C1-C10.
6. The process for producing a diaryl acetate-based compound according to claim 1, wherein: the solvent in the step (1) is any one of acetonitrile, propionitrile, isopropyl nitrile, n-butyl nitrile, isobutyl nitrile, tert-butyl nitrile, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, ethylbenzene, p-xylene, diethyl ether, THF, dioxane and dimethoxyethane.
7. The process for producing a diaryl acetate-based compound according to any one of claims 1 to 6, wherein: in the step (1), the molar ratio of diaryl 1, 2-diketone compound, alcohol compound, trialkyl phosphite and photocatalyst is 1 (1-10): (1-3): (0.001-0.1), and the concentration of diaryl 1, 2-dione compound in the reaction solution is 0.01-1.0M.
8. The process for producing a diaryl acetate-based compound according to claim 7, wherein: the light source in the step (2) is a CFL bulb, sunlight or an LED lamp, the power range of the CFL bulb is 9-100W, the wavelength range of the LED lamp is 445-455nm, and the power is 1-10W.
9. The process for producing a diaryl acetate-based compound according to claim 7, wherein: and (3) protecting the reaction process in the step (2) by using argon or nitrogen, wherein the reaction time is 2-7 days.
10. The diaryl acetate-based compound prepared by the preparation method according to claim 8 or 9, wherein the structural formula is as follows:
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