A kind of synthetic method of the benzofuranone compound containing sulfone group
A technology of benzofuranone and synthesis method, applied in the direction of organic chemistry, etc., to achieve the effects of wide substrate range, safe operation and mild conditions
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Embodiment 1
[0033] Add 0.3 mmol 2-(4-methylphenylethynyl) phenyl alkenyl ether (M.Hu, R-J.Song and J-H, Li, Angew.Chem.Int.Ed.2015,54,608– 612), 0.6 mmol of sodium benzene sulfinate, 0.06 mmol of silver nitrate, 0.6 mmol of potassium persulfate and 3 milliliters of acetonitrile, stirred and reacted at 80 degrees Celsius at 700 rpm for 4 hours, and stopped stirring. Add 4 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, evaporate the solvent under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 8:1, and the yield was 74%.
[0034] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows figure 1 with figure 2 shown; the structural characterization data are shown below:
[0035] 1 H NMR (400MHz, CDCl ...
Embodiment 2
[0042]Add 0.3 mmol 2-thienylphenyl alkenyl ether (M.Hu, R-J. Song and J-H, Li, Angew. Chem. Int. Ed. 2015, 54, 608–612), 0.6 mmol phenylene oxide into the reaction tube Sodium sulfonate, 0.06 mmol of silver nitrate, 0.6 mmol of potassium persulfate and 3 ml of acetonitrile were stirred and reacted at 80 degrees Celsius at 700 rpm for 6 hours, and the stirring was stopped. Add 4 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, evaporate the solvent under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 5:1, and the yield was 62%.
[0043] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 with Figure 4 shown; the structural characterization data are shown below:
[0044] 1 H...
Embodiment 3
[0051] Add 0.3 mmol 5-chloro-2-phenylethynylphenyl alkenyl ether (M.Hu, R-J. Songand J-H, Li, Angew. Chem. Int. Ed. 2015, 54, 608–612), 0.6 Millimol sodium benzene sulfinate, 0.06 mmol silver nitrate, 0.6 mmol potassium persulfate and 4 milliliters of acetonitrile were stirred and reacted at 80 degrees Celsius at 700 rpm for 4 hours, and the stirring was stopped. Add 4 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, evaporate the solvent under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 6:1, and the yield was 62%.
[0052] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 5 with Image 6 shown; the structural characterization data are shown below:
[0053] 1 H NMR (400...
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