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Method for preparing 2-methyl-1,3-dicarbonyl derivative

A technology of dicarbonyl and derivatives, which is applied in the field of preparation of organic compounds, can solve the problems of unfavorable environment of chemical reagents, harsh reaction conditions, inconvenient operation, etc., and achieve the effect of being conducive to safe production, easy availability of raw materials, and avoiding waste of raw materials

Inactive Publication Date: 2016-01-20
翁后科
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] The method requires the precious metal rhodium as a catalyst, Et 2 Zn is used as a reaction reagent, resulting in waste of raw materials, high cost, and excessive chemical reagents are not good for the environment
[0023] In the existing synthesis technology of 2-methyl-1,3-dicarbonyl derivatives, precious metals need to be used as catalysts, the reaction conditions are harsh, the reaction is highly corrosive, the pollution is large, the risk is high, and the operation is inconvenient.

Method used

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  • Method for preparing 2-methyl-1,3-dicarbonyl derivative
  • Method for preparing 2-methyl-1,3-dicarbonyl derivative
  • Method for preparing 2-methyl-1,3-dicarbonyl derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Synthesis of 2-methyl-1,3-diphenyl-1,3-propanedione

[0051] Using 1,3-diphenyl-1,3-propanedione and tert-butyl peroxybenzoate as raw materials, the reaction steps are as follows:

[0052] Add 1,3-diphenyl-1,3-propanedione (0.22g, 1mmol), tert-butyl peroxybenzoate (0.58g, 3mmol), CuCl (0.01g, 0.1mmol) and 2mL acetic acid, react at 120°C;

[0053] TLC tracking reaction until complete completion;

[0054] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 40:1) to obtain the target product (90% yield). The analytical data of the product are as follows: 1 HNMR (400MHz, CDCl 3 ): δ 7.98 (dt, J =8.6,1.7Hz,4H),7.70–7.52(m,2H),7.53–7.41(m,4H),5.30(q, J =7.0Hz,1H),1.63(d, J =7.0Hz, 3H).

Embodiment 2

[0055] Example 2: Synthesis of 1-(4-methylphenyl)-2-methyl-3-phenyl-1,3-propanedione

[0056] Using 1-(4-methylphenyl)-3-phenyl-1,3-propanedione and tert-butyl peroxybenzoate as raw materials, the reaction steps are as follows:

[0057] Add 1-(4-methylphenyl)-3-phenyl-1,3-propanedione (0.24 g, 1 mmol), tert-butyl peroxybenzoate (0.58 g, 3 mmol), CuCl (0.01g, 0.1mmol) and 2mL acetic acid, react at 110°C;

[0058] TLC tracking reaction until complete completion;

[0059] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 40:1) to obtain the target product (yield 85%). The analytical data of the product are as follows: 1 HNMR (400MHz, CDCl 3 ): δ 7.97 (dd, J =5.2,3.4Hz,2H),7.89(d, J =8.2Hz,2H),7.61–7.53(m,1H),7.46(t, J =7.7Hz,2H),7.27(d, J =8.2Hz,2H),5.27(q, J =7.0Hz,1H),2.42(s,3H),1.61(d, J =7.0Hz, 3H).

Embodiment 3

[0060] Example 3: Synthesis of 1-(4-methoxyphenyl)-2-methyl-3-phenyl-1,3-propanedione

[0061] Using 1-(4-methoxyphenyl)-3-phenyl-1,3-propanedione and tert-butyl hydroperoxide as raw materials, the reaction steps are as follows:

[0062] Add 1-(4-methoxyphenyl)-3-phenyl-1,3-propanedione (0.25 g, 1 mmol), tert-butyl hydroperoxide (0.27 g, 3 mmol), CuCl (0.01g, 0.1mmol) and 2mL acetic acid, react at 100°C;

[0063] TLC tracking reaction until complete completion;

[0064] The crude product obtained after the reaction was separated by column chromatography (petroleum ether:ethyl acetate=40:1) to obtain the target product (yield 88%). The analytical data of the product are as follows: 1 HNMR (400MHz, CDCl 3 ): δ 8.08–7.76(m,4H),7.56(dd, J =10.5,4.2Hz,1H),7.45(t, J =7.7Hz,2H),7.10–6.73(m,2H),5.23(q, J =7.0Hz,1H),3.86(s,3H),1.60(d, J =7.0Hz, 3H).

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Abstract

The invention discloses a method for preparing a 2-methyl-1,3-dicarbonyl derivative. A 1,3-dicarbonyl derivative serves as an initiator, raw materials are easy to obtain, and a great variety of raw materials are available. The product obtained through the method has high type diversity and can be used directly or used for other further reactions. Besides, only organic peroxides and a catalytic amount of inorganic copper salt are used, so that cost is low. According to the method, a reaction is conducted in air, reaction conditions are mild, pollution is small, reaction time is short, the yield of the target product is high, reaction operation and aftertreatment are easy, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of 2-methyl-1,3-dicarbonyl derivatives. Background technique [0002] 2-Methyl-1,3-dicarbonyl derivatives are an important class of pharmaceutical intermediates, such as 2-methyl-1,3-cyclopentanedione and 2-methyl-1,3-cyclohexanedione It can be used in the synthesis of steroid drugs. Rosevastatin is currently the best and safest hypolipidemic drug on the market developed by AstraZeneca, 2-methyl-1-(4-fluorophenyl)-3-isopropyl-1,3-di Ketones can be used in the synthesis of rosuvastatin. [0003] U.S. Patent US5260440 discloses rosuvastatin (Formula I) and its synthesis method. One of the key intermediates for the synthesis of rosuvastatin is 5-(formyl)-4-(4-fluorophenyl)-6-isopropyl -2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine (formula II), but the prior art for synthesizing this intermediate has shortcomings such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/784C07C49/84C07C49/813C07C49/807C07C49/76C07C49/12C07C49/167C07C49/395C07C49/403C07C45/68C07C255/56C07C255/17C07C253/30C07C69/716C07C67/343
CPCC07C45/68C07C67/343C07C253/30C07C49/784C07C49/84C07C49/813C07C49/807C07C49/76C07C49/12C07C49/167C07C49/395C07C49/403C07C255/56C07C255/17C07C69/716Y02A50/20
Inventor 邹建平周少方张沛之张国玉周鹏俊李成坤
Owner 翁后科
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