Method for preparing trifluoromethyl functionalized 1,3-dioxolane

A technology of trifluoromethyl and dioxopentacycline, which is applied in the field of preparation of trifluoromethyl functionalized 1,3-dioxopentacycline, can solve problems such as difficulties in the synthesis process and inconformity with the principle of atom economy, and achieve The effect of broad application prospects

Active Publication Date: 2017-02-22
SHIHEZI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the synthesis process of this kind of compound is relatively difficult, multi-step method is required to be prepared, which does not conform to the principle of atom economy, so it is rarely reported in the literature

Method used

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  • Method for preparing trifluoromethyl functionalized 1,3-dioxolane

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Experimental program
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Effect test

Embodiment 1

[0015] 2,2,2-Trifluoroacetophenone (1.0mmol), ethyl propiolate (0.5mmol), AgF (0.05mmol), K 2 CO 3 (0.1 mmol) and DMSO (1 mL) were added to a Schrink flask, and the reaction was stirred at room temperature for 24 h, followed by TLC. After the reaction was completed, 15 mL of saturated brine was added to quench the reaction, and the reaction mixture was extracted with dichloromethane (15 mL×3). The organic phases were combined and concentrated using a rotary evaporator to obtain a crude product, which was obtained by column chromatography. The eluent used in column chromatography was petroleum ether: ethyl acetate (100:1), and the structure of the product was identified by NMR and high-resolution mass spectrometry. The separation yield of 1a reaches 43%, and the separation yield of 2a reaches 45%.

Embodiment 2

[0017] 2,2,2-Trifluoroacetophenone (1.0mmol), tert-butyl propiolate (0.5mmol), Ag 2 CO 3 (0.05 mmol), KOH (0.1 mmol) and DMA (1 mL) were added to a Schlink flask, and the reaction was stirred at room temperature for 24 h, followed by TLC. After the reaction was completed, 15 mL of saturated brine was added to quench the reaction, and the reaction mixture was extracted with dichloromethane (15 mL×3). The organic phases were combined and concentrated using a rotary evaporator to obtain a crude product, which was obtained by column chromatography. The eluent used in column chromatography was petroleum ether: ethyl acetate (100:1), and the structure of the product was identified by NMR and high-resolution mass spectrometry. The separation yield of 1a was 41%, and the separation yield of 2a was 42%.

Embodiment 3

[0019] 1-(4'-tolyl)-2,2,2-trifluoroethanone (1.0mmol), tert-butyl propiolate (0.5mmol), AgOOCH 2 CH 3 (0.05 mmol), NaHCO 3 (0.1 mmol) and DMA (1 mL) were added into a Schlinker bottle, and the reaction was stirred at room temperature for 24 h, and the reaction was tracked by thin-layer chromatography. After the reaction was completed, 15 mL of saturated brine was added to quench the reaction, and the reaction mixture was extracted with dichloromethane (15 mL × 3) to extract the reaction product. The organic phases were combined and concentrated using a rotary evaporator to obtain a crude product. The eluent used in column chromatography was petroleum ether: ethyl acetate (100:1), and the structure of the product was identified by NMR and high-resolution mass spectrometry. The separation yield of 1f reaches 40%, and the separation yield of 2f reaches 45%.

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Abstract

The invention discloses a method for preparing trifluoromethyl functionalized 1,3-dioxolane. The method comprises the following procedures: subjecting trifluoromethyl ketone and a terminal alkyne compound, which are in the mole ratio of 2: 1, to a stirring reaction for 24 to 36 hours under the conditions of a silver catalyst, an alkaline environment and an organic solvent; and adding saturated common salt water to quench the reaction, carrying out extraction on the reacted mixture for 2 to 3 times by using dichloromethane, mixing organic phases, carrying out rotary evaporation to remove the organic solvent, and carrying out column chromatography separation, thereby obtaining the trifluoromethyl functionalized 1,3-dioxolane. The method disclosed by the invention for simply and efficiently preparing the trifluoromethyl functionalized 1,3-dioxolane is developed for the first time. The method has an extensive application prospect in the aspects of synthesis and the like of medicines, pesticides and organic functional materials.

Description

technical field [0001] The invention relates to the technical field of organic compound catalytic chemistry, in particular to a preparation method of trifluoromethyl functionalized 1,3-dioxane. Background technique [0002] Trifluoromethyl-functionalized 1,3-dioxane compounds are an important class of organic synthesis intermediates in drugs, pesticides and organic functional materials. The reason why these compounds are important is that in 1,3-diox At the same time as the pentacyclic ring is formed, a CF3 group is introduced into the ring, which is a group with potential biological activity and special physical properties, because currently 30% of synthetic drugs and 20% of pesticides contain fluorine atom. Because the synthesis process of this kind of compound is relatively difficult, multi-step method is required to be prepared, which does not conform to the principle of atom economy, so it is rarely reported in the literature. Contents of the invention [0003] Aimi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/30
CPCC07D317/30
Inventor 刘宁代斌王磊
Owner SHIHEZI UNIVERSITY
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