Chromane compound and preparation method thereof
A compound and chromane technology, applied in the field of trifluoromethylated chromane compounds and their preparation, to achieve the effects of mild reaction conditions and simple operation
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[0021] Described a kind of chromane compound and preparation method thereof, comprises the following steps:
[0022] Disperse the olefin of structure (I), the trifluoromethyl reagent of structure (II) and the oxidizing agent in the solvent, heat and stir to obtain the chromane compound with structure (III):
[0023]
[0024] The specific structure of III is:
[0025]
[0026] Described oxidizing agent is potassium persulfate, sodium persulfate or ammonium persulfate;
[0027] The solvent is dimethylsulfoxide, acetonitrile, 1,2-dichloroethane, N,N-dimethylformamide, tetrahydrofuran, ethanol, acetone, 1,4-dioxane or ethyl acetate a kind of
[0028] The mol ratio of described olefin and trifluoromethyl reagent is 1:1.5-1:2;
[0029] The molar ratio of the olefin to the oxidizing agent is 1:1-1:3;
[0030] Described reaction temperature is 25 ℃-60 ℃;
[0031] The reaction time is 12-20h.
Embodiment 1
[0033] In a clean and dry 20mL Schlenk reaction tube, add 1mmol of 4-tert-butyl-enylphenol, 1.6mmol of sodium trifluoromethanesulfinate, 3mmol of potassium persulfate, and then add 4mL of dimethyl Using sulfoxide as a solvent, the reaction tube was sealed and placed in an oil bath at 50° C. for heating for 20 hours. After the reaction, ethyl acetate was added to extract the reaction mixture, and then water was added to extract the reaction solvent. The organic phase was spin-dried by a rotary evaporator, and the resulting residue was passed through a silica gel column with petroleum ether and ethyl acetate as eluents. After separation, the target product was obtained as a colorless oily liquid with a yield of 50%.
[0034] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the NMR fluorine spectrum is shown as Figure 1b As shown, the carbon NMR spectrum is as Figure 1c shown. It can be confirmed fr...
Embodiment 2
[0036] In a clean and dry 20mL Schlenk reaction tube, add 1mmol of 4-cyano-enbutylphenol, 1.8mmol of sodium trifluoromethanesulfinate, 3mmol of potassium persulfate, and then add 4mL of dimethyl sulfide Sulfone was used as a solvent, and the reaction tube was sealed and placed in an oil bath at 60° C. for heating for 18 hours. After the reaction, ethyl acetate was added to extract the reaction mixture, and then water was added to extract the reaction solvent. The organic phase was spin-dried by a rotary evaporator, and the resulting residue was passed through a silica gel column with petroleum ether and ethyl acetate as eluents. After separation, the target product was obtained as a colorless oily liquid with a yield of 41%.
[0037] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 2a As shown, the NMR fluorine spectrum is shown as Figure 2b As shown, the carbon NMR spectrum is as Figure 2c shown. It can be ...
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