Method for synthesizing 4-polyfluoroalkyl-3,5-dicarbonyl pyrazole compound
A technology of dicarbonylpyrazole and polyfluoroalkyl, which is applied in the field of chemical synthesis of organic fluorine, can solve the problems of extreme reaction conditions, narrow application range, and few methods, and achieve product diversification, good adaptability, and easy operation Effect
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Embodiment 1
[0031] Under a nitrogen protective atmosphere, in a 10 mL reaction tube with a polytetrafluoroethylene magnetic stirrer, add 0.3 mmol of 4-methylacetophenone, 0.05 mmol of cuprous cyanide, and 2000 mmol of N , N -Dimethylformamide, 0.9 mmol of ethyl diazotrifluoroacetoacetate, and finally 0.9 mmol of 1,8-diazabicycloundec-7-ene, in an oil bath at 50°C Stir the reaction in a closed system for 12 h, then cool to room temperature, dilute the reaction mixture with ethyl acetate, wash with saturated ammonium chloride solution, and wash the organic phase with anhydrous MgSO 4 Dry, filter and remove the solvent by rotary evaporation, and then use the mixed system of n-pentane and ethyl acetate in a volume ratio of 2:1 as the eluent to obtain 3-(4-methylbenzoyl) through silica gel column chromatography )-4-(trifluoromethyl)-1 H - Ethyl pyrazole-5-carboxylate (isolated yield 70%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.58 –7.14 (m, 4H), 4.47 (q, J = 7.2 Hz, 2H), 2.55 (s, 3H), 1.42 (t, J...
Embodiment 2
[0033] Under a nitrogen protective atmosphere, in a 10 mL reaction tube with a polytetrafluoroethylene magnetic stirrer, add 0.3 mmol of 2-methylacetophenone, 0.05 mmol of cuprous cyanide, and 2000 mmol of N , N -Dimethylformamide, 0.9 mmol of ethyl diazotrifluoroacetoacetate, and finally 0.9 mmol of 1,8-diazabicycloundec-7-ene, in an oil bath at 50°C Stir the reaction in a closed system for 12 h, then cool to room temperature, dilute the reaction mixture with ethyl acetate, wash with saturated ammonium chloride solution, and wash the organic phase with anhydrous MgSO 4 Dry, filter and remove the solvent by rotary evaporation, then use the mixed system of n-pentane and ethyl acetate at a volume ratio of 2:1 as the eluent, and obtain 3-(2-methylbenzoyl) through silica gel column chromatography )-4-(trifluoromethyl)-1 H - Ethyl pyrazole-5-carboxylate (isolated yield 83%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.79(dd, J = 8.3, 1.9 Hz, 2H), 7.48 – 6.76 (m, 2H), 4.46 (q, J = 6.9 Hz...
Embodiment 3
[0035] Under a nitrogen protective atmosphere, in a 10 mL reaction tube with a polytetrafluoroethylene magnetic stirrer, add 0.3 mmol of 2,4-dimethylacetophenone, 0.05 mmol of cuprous cyanide, and 2000 mmol of N , N -Dimethylformamide, 0.9 mmol of ethyl diazotrifluoroacetoacetate, and finally 0.9 mmol of 1,8-diazabicycloundec-7-ene, in an oil bath at 50°C Stir the reaction in a closed system for 12 h, then cool to room temperature, dilute the reaction mixture with ethyl acetate, wash with saturated ammonium chloride solution, and wash the organic phase with anhydrous MgSO 4 Dry, filter and remove the solvent by rotary evaporation, then use the mixed system of n-pentane and ethyl acetate at a volume ratio of 2:1 as the eluent, and separate 3-(2,4-dimethyl Benzoyl)-4-(trifluoromethyl)-1 H - Ethyl pyrazole-5-carboxylate (isolated yield 45%). 1 H NMR (400 MHz, CDCl 3 )δ 7.36 (d, J = 7.9 Hz, 1H), 7.15 (s, 1H), 7.05 (d, J = 8.0 Hz, 1H), 4.48 (dd, J = 7.2, 1.4 Hz, 2H), 2.56...
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