Propargyl sulfone compound and preparation method and application thereof
A technology of propargyl sulfone and compounds, which is applied in the field of organic chemical synthesis, can solve the problems of limited application, and achieve the effect of high atom economy and wide application range of substrates
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Embodiment 1
[0027] A. At -78°C, add 1.32mL n-hexane solution containing n-butyllithium into 6mL anhydrous tetrahydrofuran solution containing phenylacetylene, stir for 1 hour, add 0.305mL benzaldehyde, the reaction equation is:
[0028]
[0029] Obtain reaction mixture; Wherein, the mol ratio of described n-butyllithium, phenylacetylene is 1:1;
[0030] B. The reaction mixture was turned to room temperature and stirred for 1 hour, quenched with saturated ammonium chloride aqueous solution, the resulting aqueous solution was extracted with (2-15) mL ethyl acetate, and the combined organic layer was washed with 20 mL saturated brine;
[0031] C. After drying the organic layer with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography with petroleum ether and ethyl acetate (PE / EA) to obtain light yellow oily liquid 1,3-diphenyl -2-propyn-1-ol, yield 95%.
Embodiment 2
[0033] Same as Example 1, the difference is that the concentration of n-butyllithium in the n-hexane solution is 3.3mmol / 1.32mL; the concentration of phenylacetylene in the tetrahydrofuran solution is 3.3mmol / 6mL, and the light yellow oily liquid 1 is obtained. , The yield of 3-diphenyl-2-propyn-1-ol was 97%.
Embodiment 3
[0035] (1) Add 1,3-diphenyl-2-propyn-1-ol (0.3mmol) into a 10ml reaction tube, add 2ml of acetonitrile, then add p-toluenesulfinic acid (0.45mmol), and stir at room temperature 12h, the reaction equation is:
[0036]
[0037] (2) After TLC monitors that the reaction is complete, the reaction solution is transferred to a 25ml heart-shaped bottle, and acetonitrile is removed with a vacuum rotary evaporator, and the product is separated by column chromatography. The developing agent is petroleum ether / ethyl acetate=95:5, and the product is Light yellow solid 1,3-diphenyl-3-p-toluenesulfonyl-1-propyne, yield 91%.
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