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Preparation method of alpha-acyloxy ketone compound

A technology for acyloxy ketones and dicarbonyl compounds is applied in the field of preparation of α-acyloxy ketone compounds, and can solve the problems of harsh reaction conditions, expensive acyloxylation reagents, complicated operation and the like, and achieves mild reaction conditions, Good industrial application prospects, simple construction effect

Pending Publication Date: 2021-08-03
WEINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The synthetic method of known α-acyloxy ketone has following several kinds: 1), compounds such as hypervalent iodine reagent oxidized ketone, propargyl alcohol and terminal alkyne, 2), the nucleophilic substitution reaction of α-halogenated ketone and carboxylic acid ; 3), the intramolecular acyloxy transfer reaction of enamide, etc.; the above-mentioned three methods all have the problems of harsh reaction conditions, complicated operation and expensive prices of acyloxylation reagents; therefore, it is necessary to develop some novel and efficient synthetic The α-acyloxyketone method is of great significance

Method used

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  • Preparation method of alpha-acyloxy ketone compound
  • Preparation method of alpha-acyloxy ketone compound
  • Preparation method of alpha-acyloxy ketone compound

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Embodiment 1

[0021] The embodiment of the present invention provides a preparation method of α-acyloxyketone compound, specifically, take a dry reaction tube, add 0.4mmol ethyl benzoylacetate, 0.4mmol sodium benzoate, 2mL dimethyl sulfoxide and 0.4mmol carbon tetrabromide, stirred and reacted at a temperature of 20-30°C for 0.5h to obtain a mixture; then 5mL of water was added to the mixture to quench, and extracted three times with 10mL of ethyl acetate, so that the organic phase Separate from the water phase, combine the extracts, wash the organic phase with saturated brine, and dry with anhydrous sodium sulfate; then use a rotary evaporator to remove the organic solvent to obtain a crude product of α-acyloxyketone compound, and use a 200-300-mesh Silica gel was separated by column chromatography, and the eluent was prepared from petroleum ether and ethyl acetate at a volume ratio of 10:1. The crude product was separated by column chromatography to obtain a pure α-acyloxyketone compound w...

Embodiment 2

[0029] The embodiment of the present invention provides a preparation method of α-acyloxyketone compound, specifically, take a dry reaction tube, add 0.4mmol dibenzoylmethane, 0.4mmol sodium benzoate, 2mL dimethylmethylene Sulfone and 0.4mmol N-bromosuccinimide were stirred and reacted at a temperature of 20 to 30°C for 0.5h to obtain a mixture, then 5mL of water was added to the mixture to quench, and extracted three times with 10mL of ethyl acetate, thereby The organic phase and the aqueous phase were separated, the extracts were combined, the organic phase was washed with saturated brine, and dried with anhydrous sodium sulfate; ~300 mesh silica gel was separated by column chromatography. The eluent was prepared from petroleum ether and ethyl acetate at a volume ratio of 10:1. The crude product was separated by column chromatography to obtain a pure compound of α-acyloxyketone. The yield 88%. Its reaction formula is as follows:

[0030]

[0031] The reaction product th...

Embodiment 3

[0037] The embodiment of the present invention provides a preparation method of α-acyloxyketone compound, specifically, take a dry reaction tube, add 0.4mmol N-acetylacetonate morpholine, 0.4mmol sodium benzoate, 2mL N,N - Dimethylformamide and 0.4mmol carbon tetrabromide, stirred and reacted at a temperature of 20 to 30°C for 0.5h to obtain a mixture, then quenched by adding 5mL of water to the mixture, and extracted three times with 10mL of ethyl acetate, Thereby, the organic phase and the aqueous phase are separated, the extracts are combined, the organic phase is washed with saturated brine, and dried with anhydrous sodium sulfate; 200-300 mesh silica gel was separated by column chromatography. The eluent was prepared from petroleum ether and ethyl acetate at a volume ratio of 10:1. The crude product was separated by column chromatography to obtain a pure compound of α-acyloxyketone. rate of 77%. Its reaction formula is as follows:

[0038]

[0039] The reaction produ...

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Abstract

The invention discloses a preparation method of an alpha-acyloxy ketone compound, which comprises the following steps of adding a 1, 3-dicarbonyl compound, carboxylate and a catalyst alkyl halide into an organic solvent, and stirring and reacting for 0.5-1 hour at the temperature of 20-30 DEG C to obtain a reaction product, namely a mixture, performing purification treatment on the mixture to obtain alpha-acyloxy ketone, wherein the molar ratio of the 1, 3-dicarbonyl compound to the carboxylate to the alkyl halide is 1: 1: 1. According to the method, carboxylate with low cost is selected as an acyloxylation reagent, reaction conditions are mild and green, a 1, 3-dicarbonyl compound is taken as a raw material, and a novel method for efficiently, simply and conveniently constructing a C-O bond is successfully realized through activation of a carbonyl alpha-position C-H bond and subsequent cascade reaction, so that a series of alpha-acyloxyketone compounds are obtained.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of α-acyloxyketone compounds. Background technique [0002] α-acyloxyketone is a very important structural skeleton, which widely exists in drug molecules and biologically active natural products. In addition, α-acyloxyketone is an important class of synthetic precursors of drug molecules. In organic synthesis Has a wide range of applications. [0003] The synthetic method of known α-acyloxy ketone has following several kinds: 1), compounds such as hypervalent iodine reagent oxidized ketone, propargyl alcohol and terminal alkyne, 2), the nucleophilic substitution reaction of α-halogenated ketone and carboxylic acid ; 3), the intramolecular acyloxy transfer reaction of enamide, etc.; the above-mentioned three methods all have the problems of harsh reaction conditions, complicated operation and expensive prices of acyloxylation reagents; ...

Claims

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Application Information

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IPC IPC(8): C07C67/035C07C69/78C07D295/185C07C69/738C07D333/24C07B41/12
CPCC07C67/035C07D295/185C07D333/24C07B41/12C07C69/78C07C69/738
Inventor 周小强
Owner WEINAN NORMAL UNIV
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