Method for synthetizing 2-trifluoromethyl oxazole compound

A technology of trifluoromethyloxazole and a synthetic method, applied in directions such as organic chemistry, can solve the problems of unobtainable raw materials, harsh conditions, complicated steps and the like, and achieves the effects of good adaptability, easy operation and high yield

Inactive Publication Date: 2018-05-15
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the methods for synthesizing 2-trifluoromethyloxazole compounds have disadvantages such as cumbersome steps, difficult raw materials, and harsh conditions.

Method used

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  • Method for synthetizing 2-trifluoromethyl oxazole compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Put a polytetrafluoroethylene magnet in a 25 mL reaction tube, add 1.0 mmol acetophenone O-acetyl oxime, 2.0 mmol trifluoroacetic anhydride, 1.0 mmol tellurium powder, 0.2 mmol iodine and 3.0 mL toluene, 120 °C After stirring and reacting in a closed system for 4 h, the resulting reaction solution was extracted three times with ethyl acetate, the organic phases were combined, washed with water and then evaporated to remove the organic solvent; the obtained crude product was purified by silica gel column chromatography using n-pentane as the eluent. 4-Phenyl-2-(trifluoromethyl)oxazole was isolated (95% yield). 1 H NMR (400 MHz, CDCl 3 ) δ 8.03 (s, 1H), 7.79 (d, J = 7.6 Hz, 2H), 7.44(dt, J = 22.5, 7.0 Hz, 3H). 19 F NMR (376 MHz, CDCl 3 ) δ -65.9 (s, 3F). 13 C NMR (101 MHz, CDCl 3 ) δ 150.9 (q, J = 44.0 Hz), 142.1 (s), 135.4 (q, J = 1.2 Hz), 129.2 (s), 129.1 (s), 128.9 (s), 125.8 (s), 116.5 (q, J = 270.7 Hz). GC-MS m / z 213 (M + ).

Embodiment 2

[0022] Put a PTFE magnet in a 25 mL reaction tube, add 1.0 mmol 4-methylacetophenone O-acetyl oxime, 2.0 mmol trifluoroacetic anhydride, 1.0 mmol tellurium powder, 0.2 mmol iodine and 3.0 mL Toluene, stirred and reacted in a closed system at 120°C for 4 h, the resulting reaction solution was extracted three times with ethyl acetate, the organic phases were combined, washed with water, and then rotary evaporated to remove the organic solvent; the obtained crude product used n-pentane as the eluent, passed Silica gel column chromatography gave 4-(p-tolyl)-2-(trifluoromethyl)oxazole (98% yield). 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 (s, 1H), 7.68 (d, J = 8.2 Hz, 2H),7.28 (d, J = 8.3 Hz, 2H), 2.42 (s, 3H). 19 F NMR (376 MHz, CDCl 3 ) δ -65.8 (s,3F). 13 C NMR (101 MHz, CDCl 3 ) δ 150.9 (q, J = 43.9 Hz), 142.1 (s), 139.1 (s), 134.9 (q, J = 1.2 Hz), 129.6 (s), 126.40 (s), 125.7 (s), 116.5 (q, J = 270.6Hz), 21.3 (s).. GC-MS m / z 227 (M + ).

Embodiment 3

[0024] Put a polytetrafluoroethylene magnet in a 25 mL reaction tube, add 1.0 mmol 4-methylthioacetophenone O-acetyl oxime, 2.0 mmol trifluoroacetic anhydride, 1.0 mmol tellurium powder, 0.2 mmol iodine and 3.0 mL of toluene, stirred and reacted in a closed system at 120°C for 4 h, the resulting reaction solution was extracted three times with ethyl acetate, the organic phases were combined, washed with water and then evaporated to remove the organic solvent; the obtained crude product was obtained with n-pentane as eluent, 4-(p-Methylthiobenzene)-2-(trifluoromethyl)oxazole was obtained by silica gel column chromatography (yield 73%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.02 (s, 1H), 7.82 – 7.63 (m, 2H), 7.32 (d, J = 8.2 Hz, 2H), 2.54 (s, 3H). 19 F NMR (376 MHz, CDCl 3 ) δ -65.8 (s,3F). 13 C NMR (101 MHz, CDCl 3 ) δ 150.9 (q, J = 44.2 Hz), 141.7 (s), 140.0 (s), 135.1 (d, J = 0.9 Hz), 126.50\ (s), 126.2 (s), 125.8 (s), 116.5 (q, J = 270.6Hz), 15.5 (s). GC-MS m / z 259 (M ...

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Abstract

The invention discloses a method for synthetizing a 2-trifluoromethyl oxazole compound. According to the method, trifluoroacetic anhydride is used as a reaction reagent; an oxime ester derivative is used as a reaction substrate; a tellurium compound and iodine are used as catalysts; in a solvent, heating is performed at 110 to 120 DEG C; stirring reaction is performed for 1 to 8h; the 2-trifluoromethyl oxazole compound is prepared. The synthesis method has the advantages that the yield is high; the raw materials can be easily obtained; the operation is simple and convenient; the functional group universality is good, and the like. Good industrial application prospects are realized.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing 2-trifluoromethyloxazole compounds. Background technique [0002] Organic fluorine-containing compounds have been widely used in the fields of medicine, pesticides and materials, mainly because the fluorine-containing groups have strong electron-attracting properties and high lipophilicity, and their introduction into organic molecules often causes organic molecules to decompose. Physicochemical properties changed significantly. For example, introducing a trifluoromethyl group into a drug molecule often significantly changes the lipid solubility of the parent compound and enhances the metabolic stability of the molecule. Therefore, the synthesis of trifluoromethyl-containing compounds is of great significance. [0003] Oxazole compounds are important heterocyclic compounds, which have antibacterial, antiviral, anticancer and other biologic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32C07D413/04
CPCC07D263/32C07D413/04
Inventor 翁志强罗贝贝童栎超
Owner FUZHOU UNIV
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