Preparation method of organoboron compound and preparation method of β-hydroxyorganoboron compound
A compound and organoboron technology, applied in the field of compound synthesis, can solve the problems of high residue, difficult to remove and high content, and achieve the effect of simple operation, rich source of raw materials and easy method
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Embodiment 1
[0065] A preparation method of organoboron compound II-1, the steps are:
[0066]
[0067] A. Add chitosan-supported copper sulfate catalyst (CS@CuSO 4 ) 5mg, add 2.0mL water;
[0068] B. To the above system, add starting material I-1 (38.4mg, 0.2mmol) and pinacol diborate (B 2 (pin) 2 ) (60.9mg, 0.24mmol);
[0069] C, the whole reaction system was stirred at room temperature for 12 hours to react;
[0070] D, after the reaction finishes, filter the whole reaction system, wash with tetrahydrofuran 3mL,
[0071] E. After separating the organic phase, use anhydrous Na 2 SO 4 Dry, filter and remove solvent by rotary evaporation. The residue was purified by column chromatography with ethyl acetate / petroleum ether mixed solvent = 6:1 to obtain 38.3 mg of II-1 with a yield of >99%.
[0072] 1 H NMR (400MHz); δ=7.67(s,1H),7.40-7.27(m,5H),3.80(s,3H),2.17-2.09(m,2H),1.23(s,12H).
[0073] 13 C NMR (100MHz);
[0074] A preparation method of compound III-1, the steps are: ...
Embodiment 2
[0084] A preparation method of compound III-2, the steps are:
[0085]
[0086] A. Add chitosan-supported copper sulfate catalyst (CS@CuSO 4 )5mg, add 2.0mL water.
[0087] B, in step A, add starting material I-2 (38.4mg, 0.2mmol) and diboronic acid pinacol ester (B) successively successively respectively 2 (pin) 2 ) (60.9 mg, 0.24 mmol). The whole reaction system was stirred at room temperature for 12 hours to react.
[0088] C. After the reaction, the whole reaction system was filtered, washed with 3 mL of tetrahydrofuran, and sodium perborate tetrahydrate (244 mg, 0.8 mmol) was directly added to the residue, and the whole system was stirred at room temperature for 4 hours.
[0089] D. Add 3 mL of ethyl acetate to the above system to dilute, extract with ethyl acetate (3×10 mL), separate the organic phase, and use anhydrous Na 2 SO 4Dry, filter and remove solvent by rotary evaporation. The residue was purified by column chromatography with ethyl acetate / petroleum e...
Embodiment 3
[0094] Preparation of Compound III-3:
[0095]
[0096] Chitosan-supported copper sulfate catalyst (CS@CuSO 4 ) 5 mg, add 2.0 mL of water. To the above system, the starting material I-3 (48.5 mg, 0.2 mmol) and pinacol diboronate (B 2 (pin) 2 ) (60.9 mg, 0.24 mmol). The whole reaction system was stirred at room temperature for 12 hours to react. After the reaction, the entire reaction system was filtered, washed with 3 mL of tetrahydrofuran, and sodium perborate tetrahydrate (244 mg, 0.8 mmol) was directly added to the residue, and the entire system was stirred at room temperature for 4 hours. Add 3 mL of ethyl acetate to the above system for dilution, extract with ethyl acetate (3×10 mL), separate the organic phase, and wash with anhydrous Na 2 SO 4 Dry, filter, and remove solvent by rotary evaporation. The residue was purified by ethyl acetate / petroleum ether mixed solvent = 6:1 column chromatography to obtain 41.9 mg of III-3, with a yield of 91%.
[0097] 1 H NM...
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