A kind of copper catalyzed method for synthesizing β-keto ester
A ketoester, copper-catalyzed technology, applied in the field of synthetic chemistry, can solve the problems of unstable diketene, harsh reaction conditions, complex products, etc., and achieve the effects of good substrate universality, mild reaction conditions, and wide substrate range.
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Embodiment 1
[0023]
[0024] Into the reaction tube were sequentially added ethyl benzoyl acetate (1.0 mmol), benzyl chloride (1.0 mmol), catalyst CuI (0.05 mmol), K 2 CO 3 (0.06 mmol), then 2 mL of solvent toluene was added, and the reaction was carried out at 60° C. for 12 hours. After the reaction, the reaction solution was concentrated, and the corresponding product was obtained by column chromatography, and the isolated yield was 87%. 1 H NMR (400MHz, CDCl 3 )δ: 1.21(t, J=7.5Hz, 3H), 2.73(dd, J=5.0, 17.0Hz, 1H), 3.38(q, J=10.0Hz, 1H), 4.11(q, J=7.5Hz, 2H), 5.11(q, J=5.0Hz, 1H), 7.21~7.25(m, 1H), 7.17(d, J=4.5Hz, 4H), 7.38~7.41(m, 2H), 7.49(tt, J =1.5,7.5Hz,1H),7.98~8.00(m,2H).
Embodiment 2
[0026]
[0027] Into the reaction tube were sequentially added ethyl benzoyl acetate (1.0 mmol), 4-methylbenzyl chloride (1.2 mmol), catalyst CuI (0.05 mmol), Cs 2 CO 3 (0.08 mmol), then 2 mL of solvent toluene was added, and the reaction was carried out at 80° C. for 16 hours. After the reaction, the reaction solution was concentrated, and the corresponding product was obtained by column chromatography, and the isolated yield was 89%. 1 H NMR (400MHz, CDCl 3 )δ: 1.21(t, J=7.0Hz, 3H), 2.29(s, 3H), 2.71(dd, J=5.0, 17.0Hz, 1H), 3.36(dd, J=10.0, 17.0Hz, 1H), 4.11(q,J=7.0Hz,2H),5.07(q,J=5.0,10.0Hz,1H),7.10(d,J=8.0Hz,2H),7.19(d,J=8.0Hz,2H), 7.39 (t, J=7.5Hz, 2H), 7.39 (t, J=7.5Hz, 1H), 7.98 (d, J=7.0Hz, 2H).
Embodiment 3
[0029]
[0030] Into the reaction tube were sequentially added ethyl benzoyl acetate (1.0 mmol), 4-cyanobenzyl bromide (1.2 mmol), catalyst cuprous iodide CuI (0.05 mmol), Cs 2 CO 3 (0.10 mmol), then 2 mL of solvent toluene was added, and the reaction was carried out at 90° C. for 18 hours. After the reaction was completed, the reaction solution was concentrated, and the corresponding product was obtained by column chromatography. The isolated yield was 93%. 1 H NMR (400MHz, CDCl 3 )δ: 1.21 (t, J=7.1Hz, 3H), 2.74 (dd, J=5.5, 17.0Hz, 1H), 3.70 (dd, J=9.3, 17.0Hz, 1H), 4.11 (q, J=7.2 Hz,2H),5.18(dd,J=5.5,9.3Hz,1H),7.42~7.46(m,4H),7.54(t,J=7.4Hz,1H),7.60~7.61(m,2H),7.94 ~7.96 (m, 2H).
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