A method for preparing gamma-ketocarbonyl compounds
A technology for compound and ketone carbonyl, which is applied in the field of catalytic preparation of γ-ketocarbonyl compounds, can solve problems such as low yield, and achieve the effects of convenient storage, favorable purification, and no pollutant discharge.
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Embodiment 1
[0027]
[0028] The reaction vial was filled with DABCO (6 mmol, 672 mg), compound 1a (2 mmol, 208 mg), compound 2a (4 mmol, 456 mg), Cu(acac) 2 (0.2 mmol, 48 mg), TBHP (0.8 mL), isopropanol (8 mL). Then the system was heated at 80 °C in air for about 8 hours, quenched with saturated sodium sulfite solution, extracted with ethyl acetate (40 mL × 3), adsorbed on silica gel, spin-dried the solvent in vacuo, and passed simple flash column chromatography The product 3a was obtained with a yield of 76%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.
[0029] 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 - 7.98 (m, 2H), 7.58 - 7.55 (m, 1H),7.48 - 7.44 (m, 2H), 4.16 (q, J = 7.1 Hz, 2H), 3.31 (t, J = 6.6 Hz, 2H), 2.76(t, J = 6.6 Hz, 2H), 1.26 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 )δ198.1, 172.8, 136.5, 133.1, 128.5, 127.9, 60.6, 33.3, 28.2, 14.1; M...
Embodiment 2
[0031]
[0032] DABCO (6 mmol, 672 mg), compound 1a (2 mmol, 208 mg), compound 2a (4 mmol, 456 mg), CuI (0.2 mmol, 38 mg), TBHP (0.8 mL), and Isopropanol (8 mL). Then the system was heated at 80 °C in the air for about 8 hours, quenched with saturated sodium sulfite solution, extracted with ethyl acetate (40 mL×3), adsorbed on silica gel, spin-dried the solvent in vacuum, and obtained by simple column chromatography Product 3a was obtained in 58% yield. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.
[0033] 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 - 7.98 (m, 2H), 7.58 - 7.55 (m, 1H),7.48 - 7.44 (m, 2H), 4.16 (q,J = 7.1 Hz, 2H), 3.31 (t, J = 6.6 Hz, 2H), 2.76(t, J = 6.6 Hz, 2H), 1.26 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 )δ198.1, 172.8, 136.5, 133.1, 128.5, 127.9, 60.6, 33.3, 28.2, 14.1; MS (ESI-quadrupole): Anal. Calcd. For C 12 h 14...
Embodiment 3
[0035]
[0036] DABCO (6 mmol, 672 mg), compound 1a (2 mmol, 208 mg), compound 2a (4 mmol, 456 mg), Cu (0.2 mmol, 13 mg), TBHP (0.8 mL), and Isopropanol (8 mL). Then the system was heated at 80 °C in air for about 8 hours, quenched with saturated sodium sulfite solution, extracted with ethyl acetate (40 mL × 3), and the product 3a was obtained by simple column chromatography with a yield of 56%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.
[0037] 1 H NMR (400 MHz, CDCl 3 ) δ 8.00 - 7.98 (m, 2H), 7.58 - 7.55 (m, 1H),7.48 - 7.44 (m, 2H), 4.16 (q, J = 7.1 Hz, 2H), 3.31 (t, J = 6.6 Hz, 2H), 2.76(t, J = 6.6 Hz, 2H), 1.26 (t, J = 7.1 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 )δ198.1, 172.8, 136.5, 133.1, 128.5, 127.9, 60.6, 33.3, 28.2, 14.1; MS (ESI-quadrupole): Anal. Calcd. For C 12 h 14 o 3 +H + : 207, Found: 207;IR (neat, cm -1 ): υ2981, ...
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