Benzofuran category compound, its preparing method and usage
A technology of benzopyran and compounds, which is applied in the synthesis of benzopyran compounds and the preparation of anti-type II diabetes drugs, which can solve the problems of high liver toxicity
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Embodiment 1
[0143] Example 1: 7-Benzyloxy-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester (compound 1)
[0144] 7-Hydroxy-3-coumarin carboxylate methyl ester (0.2g, 1mmol) was dissolved in N,N'-dimethylformamide (2mL), added benzyl bromide (0.36ml, 3mmol) and finely ground carbonic acid Potassium (0.5g), stirred at 70°C for 12 hours. Add water (10 mL), extract with ethyl acetate (2×10 mL), combine ethyl acetate, wash with water, and dry over anhydrous sodium sulfate. Concentrate under reduced pressure to about 5 mL. A solid precipitated after standing, and was filtered with suction to obtain 0.21 g of the title compound, with a yield of 67.7%. m.p.129-130°C. 1 H NMR (CDCl 3 ): δ=3.92(s, 3H), 5.19(s, 2H), 6.85(d, J=2.4Hz, 1H), 6.95(dd, J=8.8Hz, 2.4Hz, 1H), 7.40(m, 5H ), 7.52(d, J=8.8Hz, 1H), 8.55(s, 1H); elemental analysis, C 18 h 14 o 5 (310): calculated value C, 69.68; H, 4.52. found value C, 69.63; H, 4.51; , 1026, 794.5, 725.1, 692.3, 636.4cm -1 ; EI-MS (m / z): 310 (12, M...
Embodiment 2
[0145] Example 2: 7-Benzyloxy-2-oxo-2H-1-chromene-3-carboxylic acid (Compound 2)
[0146] Compound 1 (0.1 g, 0.32 mmol) was dissolved in ethanol (0.5 mL), 10% aqueous sodium hydroxide solution (0.5 mL) was added, and the reaction was refluxed for 1 hour. After cooling, add concentrated hydrochloric acid (0.3 mL), continue stirring for 10 minutes, add water (5 mL), suction filter the produced solid, wash the filter cake with water, and dry to obtain the title compound 0.09 g, yield 90%. m.p.196-197°C. 1 H NMR (DMSO-d6): δ=5.25(s, 2H), 7.08(dd, J=2.2Hz, 8.8Hz, 1H), 7.12(d, J=2.2Hz, 1H), 7.30-7.50(m, 5H), 7.83(d, J=8.8Hz, 1H), 8.73(s, 1H); elemental analysis, C 17 h 12 O5(296): Calculated C, 68.92; H, 4.05; Found C, 68.50; H, 4.12; 732.8cm -1 ; EI-MS (m / z): 296 (4, M + ), 91(100).
Embodiment 3
[0147] Example 3: Methyl 7-(2-phenyl)ethoxy-2-oxo-2H-1-chromene-3-carboxylate (Compound 3)
[0148] Dissolve methyl 7-hydroxy-3-coumarincarboxylate (0.6g, 3mmol) and 2-phenylethanol (0.36mL, 3mmol) in anhydrous tetrahydrofuran (60mL), add triphenylphosphine (1.2g , 4.5mmol), diethyl azodicarboxylate (0.72mL, 4.5mmol) was slowly added dropwise at 0°C, and stirred at room temperature for 24 hours. The solvent was distilled off under reduced pressure, and the residue was precipitated in methanol as a white solid, which was recrystallized from methanol to obtain 0.45 g of the title compound, with a yield of 46.3%. m.p.100-101°C. 1 H NMR (CDCl 3 ): δ=3.12(t, J=6.8Hz, 2H), 3.92(s, 3H), 4.14(t, J=7.1Hz, 2H), 6.79(d, J=2.4Hz, 1H), 6.88(dd , J=2.4Hz, 8.8Hz, 1H), 7.21-7.35(m, 5H), 7.47(d, J=8.7Hz, 1H), 8.50(s, 1H); elemental analysis, C 19 h 16 o 5 (324): calculated value C, 70.37; H, 4.94. found value C, 70.25; H, 4.93; , 1114.7, 1018.2, 835, 749.5, 738.6, 700, 594cm -1 ; EI-MS...
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