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Preparation method of ketone compound and its derivatives

A technology for ketone compounds and carboxylic acid compounds, applied in the field of preparation of ketone compounds and derivatives thereof, can solve the problems of complex operation, poor selectivity, long synthesis steps and the like

Inactive Publication Date: 2013-03-13
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have many disadvantages, such as 1) the synthesis steps are too long, and each step needs to be purified; 2) the operation is complicated; 3) the yield is low, the selectivity is poor, and there are many by-products; Large pollution; 4) Long reaction time and low efficiency

Method used

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  • Preparation method of ketone compound and its derivatives
  • Preparation method of ketone compound and its derivatives
  • Preparation method of ketone compound and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0159] The preparation and characterization of embodiment 1. diphenyl ethyl ketone

[0160]

[0161] Add 0.136g (1.0mmol) of phenylacetic acid (1.0mmol) and 0.136g (1.0mmol) of methyl benzoate to a dry 25mL schlenk bottle, 4mL of anhydrous DMF, and slowly add 2.0mL (4.0mmol, 4.0eq) at -10°C Sodium hexamethyldisilazide (NaHMDS) (5min) (4.0mmol), keep warm and continue stirring for 3.5h, monitor the reaction by TLC, after the reaction is completed, add saturated ammonium chloride (10mL) to quench the reaction, extract with ethyl acetate Three times, anhydrous Na 2 SO 4 Drying, rotary evaporation, and separation by column chromatography gave the target product as white crystals with a yield of 90%. mp=127-128℃. 1 H-NMR (300MHz, CDCl 3 ):δ8.05(s,1H),8.02(t,J=1.5Hz,1H),7.60-7.54(m,1H),7.47(t,J=7.2Hz,2H),7.37-7.24(m, 5H),4.31(s,2H); 13 C-NMR (75MHz, CDCl 3 ):δ197.7,136.6,134.6,133.2,130.2,129.5,128.7,128.7,128.6,128.5,126.9,45.5.IR(KBr,cm -1 ):3042,2904,1686,1596,1449,133...

Embodiment 2

[0162] Example 2. Preparation and characterization of 3-methoxyphenyl-2-(2-methoxyphenyl)ethanone

[0163]

[0164] Using 2-methoxyphenylacetic acid (1.0 mmol), methyl 3-methoxybenzoate (1.0 mmol), NaHMDS (4.0 mmol), saturated ammonium chloride (10 mL), by a similar method as described in Example 1 The target compound was prepared as a colorless oily liquid with a yield of 86%. 1 H-NMR (500MHz, CDCl 3 ):δ7.65(d,J=7.5Hz,1H),7.57(s,1H),7.36(t,J=7.5Hz,1H),7.26(d,J=8.0Hz,1H),7.18(d ,J=7.5Hz,1H),7.10(dd,J=8.0Hz,J=2.5Hz,1H),6.94(d,J=8.0Hz,1H),6.90(t,J=8.0Hz,1H), 4.27(s,2H),3.84(s,3H),3.79(s,3H); 13 C-NMR (75MHz, CDCl 3 ):δ198.0,157.3,137.1,132.9,131.0,129.6,128.5,128.4,128.3,123.8,120.7,110.6,55.4,40.0.IR(KBr,cm -1 ):3068,2975,2948,2841,1691,1601,1498,1194,1013.HRMS(ESI)C 16 h 16 o 3 ([M+H] + )257.1099, found 257.1173.

Embodiment 3

[0165] Example 3. Preparation and characterization of 2-(3,4-dichlorophenyl)-1-(2-furyl)-ethanone

[0166]

[0167] Using 3,4-dichlorophenylacetic acid (1.0mmol), methyl 2-furancarboxylate (1.0mmol), NaHMDS (4.0mmol), saturated ammonium chloride (10mL), the target was prepared by a method similar to that described in Example 1 Compound, light yellow oily liquid, yield 71%. 1 H-NMR (500MHz, CDCl 3 ):δ7.61(s,1H),7.40(d,J=1.5Hz,1H),7.38(d,J=8.0Hz,1H),7.25(t,J=6.0Hz,1H),7.13(dd ,J=11.5Hz,J=2.0Hz,1H),4.08(s,2H); 13 C-NMR (75MHz, CDCl 3 ):δ185.4,152.2,146.8,134.1,132.5,131.5,131.3,130.5,129.0,118.0,112.6,44.1.IR(KBr,cm -1 ):3135,2931,1672,1568,1466,1133,1033.HRMS(ESI)calcd.for C 12 h 8 C 12 o 2 ([M+H] + )254.9901, found 254.9977.

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Abstract

The invention discloses a method for preparation of a ketone compound and its derivatives by means of a carboxylic acid compound and a carboxylic ester compound in the presence of alkali. The method has the characteristics of wide substrate adaptability, short reaction time, high yield and high atom economy. The use of Lewis acid and heavy metals is avoided, the experimental operation steps are simple, the corrosion to equipment is small, and the amount of ''three wastes'' is small, so that the method is conducive to further promotion and application and industrial production.

Description

technical field [0001] The present application relates to a preparation method of ketone compounds and derivatives thereof. Specifically, the application relates to a method for preparing ketone compounds and derivatives thereof from carboxylic acid compounds and carboxylic acid ester compounds under alkaline conditions. Background technique [0002] Ketone compounds, especially aromatic ketones, are an important class of building blocks for the synthesis of pharmaceutical intermediates and the preparation of functional materials. Classical methods for the synthesis of aromatic ketones include access by oxidation of the corresponding secondary alcohols, synthesis of Weinreb ketones, and Friedel-Crafts alkylation of aromatic compounds under Lewis acid conditions. However, these methods have many disadvantages, such as 1) the synthesis steps are too long, and each step needs to be purified; 2) the operation is complicated; 3) the yield is low, the selectivity is poor, and the...

Claims

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Application Information

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IPC IPC(8): C07C49/782C07C49/84C07C49/813C07C49/213C07C45/72C07C69/738C07C67/343C07C255/40C07C253/30C07C205/45C07C201/12C07D307/46C07D213/50C07D239/22C07D401/04C07D405/04C07D237/04
Inventor 黄湧吴桂勇殷韦玉
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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