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Diaryl acetate compound and preparation method thereof

A technology for diaryl acetates and compounds, which is applied in the field of compounding and preparation of diaryl acetates, can solve the problems of harsh reaction conditions and low efficiency, and achieve the effect of mild reaction conditions and high practicability

Active Publication Date: 2020-04-10
HENAN UNIVERSITY
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Problems solved by technology

[0007] The present invention proposes a compounding and preparation method of diaryl acetate

Method used

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  • Diaryl acetate compound and preparation method thereof
  • Diaryl acetate compound and preparation method thereof
  • Diaryl acetate compound and preparation method thereof

Examples

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Comparison scheme
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Example Embodiment

[0028] Example 1

[0029] Preparation of ethyl 2,2-diphenylacetate (2a):

[0030]

[0031] Specific synthesis steps and characterization:

[0032] In a 10 ml Schlenk tube, combine benzil 1a (21 mg, 0.1 mmol, 1.0 equiv.) and P(OEt) 3 (33.2mg, 0.2 mmol, 2.0 equiv.) dissolved in DCE (1.0 ml), add EtOH (11.7 μL, 0.2 mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1 μmol), 3W LED at room temperature (450 nm) irradiate, stir and react for 48 hours, TLC detects that the reaction is complete. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same below, PE: EA = 20: 1) to obtain diaryl acetate compound 2a, 21.5 mg, 90%.

[0033] 1 H 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).

[0034] 13 C NMR (75 MHz, CDCl 3 ) 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. f...

Example Embodiment

[0037] Example 2

[0038] Preparation of 2,2-bis(4-butylphenyl)ethyl acetate (2b):

[0039]

[0040] Specific synthesis steps and characterization:

[0041] In a 10 ml Schlenk tube, combine the benzyl compound 1b (32.2 mg, 0.1 mmol, 1.0 equiv.) and P(OEt) 3 (33.2 mg, 0.2 mmol, 2.0 equiv.) dissolved in DCE (1.0 ml), add EtOH (11.7 μL, 0.2 mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1 μmol), 3W LED at room temperature (450 nm) irradiate, stir and react for 48 hours, TLC detects that the reaction is complete. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same below, PE: EA = 20: 1) to obtain diaryl acetate compound 2b, 27 mg, 77%.

[0042] 1 H 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...

Example Embodiment

[0044] Example 3

[0045] Preparation of 2,2-bis(4-chlorophenyl)ethyl acetate (2c):

[0046]

[0047] Specific synthesis steps and characterization:

[0048] In a 10 ml Schlenk tube, combine the benzil compound 1c (27.9 mg, 0.1 mmol, 1.0 equiv.) and P(OEt) 3 (33.2 mg, 0.2 mmol, 2.0 equiv.) dissolved in DCE (1.0 ml), add EtOH (11.7 μL, 0.2 mmol, 2.0 equiv.) and photocatalyst DPZ (0.0354 mg, 0.1 μmol), 3W LED at room temperature (450 nm) irradiate, stir and react for 48 hours, TLC detects that the reaction is complete. The reaction solution was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography (volume ratio, the same below, PE: EA = 20: 1) to obtain the diaryl acetate compound 2c, 22 mg, 71%.

[0049] 1 H 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).

[0050] 13 C NMR (75 MHz, CDCl 3 ) δ 171.8, 136.8, 133.4, 129.9, 128.8, 61.5, 5...

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Abstract

The invention provides a diaryl acetate compound and a preparation method, and the preparation method comprises the following steps: (1) adding a diary 1, 2-diketone compound, an alcohol compound, trialkyl phosphite and a photocatalyst into a reaction vessel, adding a solvent, and dissolving to obtain a reaction solution; (2) irradiating an reaction liquid by using a light source and stirring until the reaction is complete; and (3) after the reaction is finished, recovering the solvent under reduced pressure and purifying by column chromatography to obtain the diaryl acetate compound. Startingfrom easily available diaryl 1, 2-diketone, the method has the advantages of mild and green reaction conditions, no need of precious transition metal catalysis, economical performance, environmentalprotection, and high practicality.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for compounding and preparing diaryl acetates. Background technique [0002] Diaryl acetate structures are widely found in natural products, and many medicinal molecules such as carrelil and diazepam have this structure. Studies have shown that this type of structure has anti-virus, rheumatism, anti-tumor, central nervous activity and serotonin dopamine reuptake inhibitory activity. Related literature: (a) Xu, H.; Lv, M.; Tian, ​​X. Curr. Med. Chem.2009, 16, 327. (b) Keller, H. H.; Schaffner, R.; Carruba, M. O.; Burkard, W.P.; Pieri, M.; Bonetti, E. P.; Scherschlicht, R.; Prada, M. D.; Haefely, W.E. Adv. Biochem. Glock, D. J. Med. Chem. 1981, 24, 1013. [0003] 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-azidoacetate overcomes t...

Claims

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Application Information

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IPC IPC(8): C07C67/00C07C69/616C07C69/736
CPCC07C67/00C07C69/616C07C69/736
Inventor 魏国杨慧程仲彬赵芬琴张俨娜
Owner HENAN UNIVERSITY
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