Beta-trifluoromethyl-beta-hydroxy substituted cyclohexanone derivative and synthesis method thereof
A technology of trifluoromethyl group and synthesis method, which is applied in the field of β-trifluoromethyl-β-hydroxy-substituted cyclohexanone derivatives and the synthesis thereof, can solve the problems of few reports on the synthesis method, low yield and the like, and achieves Good industrial application prospects, high product yield, good adaptability
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Embodiment 1
[0034] A synthesis method of a β-trifluoromethyl-β-hydroxyl substituted cyclohexanone derivative in this embodiment, the specific synthesis steps are as follows:
[0035] Under a nitrogen atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 0.02 mmol cuprous chloride, 0.2 mmol 4-phenylbut-3-en-2-one oxime acetyl ester, 0.2 mmol Cesium pivalate, 0.4 mmol 1,1,1-trifluoro-3-phenylacetone, 2 ml dimethyl sulfoxide, the reaction system was stirred at 80°C for 12 hours, stopped heating and stirring, cooled to room temperature, Add water, ethyl acetate extracts the reaction solution, the ethyl acetate layer is subjected to vacuum rotary evaporation, removes the solvent, then separates and purifies by column chromatography, obtains the target product, and the column chromatography eluent used is that the volume ratio is 5: 1 sherwood oil: ethyl acetate mixed solvent; The productive rate of product is 58%.
Embodiment 2
[0037] A synthesis method of a β-trifluoromethyl-β-hydroxyl substituted cyclohexanone derivative in this embodiment, the specific synthesis steps are as follows:
[0038] Under a nitrogen atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 0.02 mmol cuprous chloride, 0.2 mmol 4-phenylbut-3-en-2-one oxime acetyl ester, 0.2 mmol Potassium carbonate, 0.2 mmol 1,1,1-trifluoro-3-phenylacetone, 2 ml dimethyl sulfoxide, the reaction system was stirred at 80°C for 12 hours, stopped heating and stirring, cooled to room temperature, and added water , extract the reaction solution with ethyl acetate, carry out the rotary evaporation of the ethyl acetate layer under reduced pressure, remove the solvent, and then separate and purify by column chromatography to obtain the target product, and the column chromatography eluent used is a volume ratio of 100:1 Petroleum ether: ethyl acetate mixed solvent; The productive rate of product is 22%.
Embodiment 3
[0040] A synthesis method of a β-trifluoromethyl-β-hydroxyl substituted cyclohexanone derivative in this embodiment, the specific synthesis steps are as follows:
[0041] Under a nitrogen atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 0.02 mmol of cuprous bromide, 0.2 mmol of 4-phenylbut-3-en-2-one oxime acetyl ester, 0.2 mmol of Cesium pivalate, 0.4 mmol 1,1,1-trifluoro-3-phenylacetone, 2 ml dimethyl sulfoxide, the reaction system was stirred at 80°C for 6 hours, stopped heating and stirring, cooled to room temperature, Add water, ethyl acetate extracts the reaction solution, the ethyl acetate layer is subjected to vacuum rotary evaporation, removes the solvent, and then separates and purifies by column chromatography to obtain the target product, and the column chromatography eluent used is a volume ratio of 10: 1's sherwood oil: ethyl acetate mixed solvent; The productive rate of product is 40%.
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