Preparation method of polysubstituted [alpha]-ketoester
A multi-substituted, ketoester technology, applied in the field of preparation of multi-substituted α-ketoesters, can solve problems such as low conversion rate and reaction yield, harsh reaction conditions, and poor substrate universality
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Embodiment 1
[0022] This Example 1 provides a method for preparing a multi-substituted α-ketoester C1, the reaction formula is as follows:
[0023]
[0024] The specific preparation process of Example 1 is as follows: into a dry 10mL reaction tube, dissolve A1 (0.12mmol, 29.6mg) in 1,4-dioxane (1mL), and add accurately weighed Cesium carbonate (0.15mmol, 48.9mg) and B1 (0.1mmol, 20.2mg), then the reaction tube was placed at room temperature and stirred for 2 hours, and thin layer chromatography (TLC) was detected. After the reaction was over, the reaction solution was transferred to the chicken heart bottle The pure target product C1 can be obtained after column chromatography (petroleum ether:ethyl acetate=15-5:1, volume ratio) with a yield of 92%.
[0025] Characterization data of C1: m.p.167-169℃. 1 H NMR (400MHz, CDCl 3 )δ7.58(d,J=7.2Hz,2H),7.49(s,1H),7.46–7.35(m,6H),7.35–7.25(m,7H),3.76(q,J=7.1Hz,2H ),0.91(t,J=7.1Hz,3H). 13 C NMR (101MHz, CDCl 3 )δ188.2, 161.3, 147.9, 146.1, 1...
Embodiment 2
[0027] This Example 2 provides a method for preparing a multi-substituted α-ketoester C2, the reaction formula is as follows:
[0028]
[0029] The specific preparation process of Example 2 is as follows: in a dry 10mL reaction tube, dissolve A2 (0.12mmol, 33.8mg) in 1,4-dioxane (1mL), and add accurately weighed Cesium carbonate (0.15mmol, 48.9mg) and B1 (0.1mmol, 20.2mg), then the reaction tube was placed at room temperature and stirred for 2 hours, detected by TLC. Chromatography (petroleum ether: ethyl acetate = 15-5:1, volume ratio) can obtain the pure target product C2 with a yield of 82%.
[0030] Characterization data of C2: m.p.173-175℃. 1 H NMR (500MHz, Chloroform-d) δ7.74–7.69(m,2H),7.67(s,1H),7.59–7.50(m,4H),7.49–7.40(m,6H),7.40–7.34(m ,2H),3.90–3.81(m,2H),1.03(t,J=7.1Hz,3H). 13 C NMR (126MHz, CDCl 3 )δ187.2,160.8,147.9,145.6,143.9,137.8,137.3,135.4,134.5,133.7,131.5,131.3,130.9,129.9,129.5,129.3,129.2,129.1,129.0,128.9,127.0,116.2,112.4,62.6,13.7 .
Embodiment 3
[0032] This embodiment 3 provides a kind of preparation method of multi-substituted α-ketoester C3, and the reaction formula is as follows:
[0033]
[0034] The specific preparation process of Example 3 is as follows: into a dry 10mL reaction tube, dissolve A3 (0.12mmol, 33.8mg) in 1,4-dioxane (1mL), and then add accurately weighed Cesium carbonate (0.15mmol, 48.9mg) and B1 (0.1mmol, 20.2mg), then the reaction tube was placed at room temperature and stirred for 2 hours, detected by TLC. Chromatography (petroleum ether:ethyl acetate=15-5:1, volume ratio) can obtain the pure target product C3 with a yield of 85%.
[0035] Characterization data of C3: m.p.153-155℃. 1 H NMR (400MHz, Chloroform-d) δ7.69–7.62(m,2H),7.59(s,1H),7.56–7.48(m,3H),7.48–7.37(m,6H),7.37–7.27(m ,3H),3.88(q,J=7.1Hz,2H),1.03(t,J=7.1Hz,3H). 13C NMR (101MHz, CDCl 3 )δ187.9,161.2,148.0,145.3,144.7,137.6,137.3,137.2,135.8,134.6,131.3,130.0,129.9,129.5,129.5,129.2,129.1,129.0,128.9,128.8,128.2,116.4,111.7,6...
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