Method for synthesizing quercetin ester from rutin through one-pot method, and product and application thereof
A technology of quercetin ester and boiling in a pot, which is applied in the direction of drug combination, organic chemistry, antineoplastic drugs, etc., can solve the problems of acid-containing wastewater polluting the environment, consuming large methanol, and high product cost, so as to achieve easy availability of reagents and reduce emissions , the effect of saving raw materials
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Embodiment 1
[0029] Synthesis of Quercetin Pentaacetate (1)
[0030] Weigh 610mg (1mmol) of rutin, add 5ml of acetic anhydride, stir with a magnetic stirrer for 0.5h, make it fully dissolved, add 5 drops of concentrated sulfuric acid, control the temperature at 65°C, reflux for 6h, monitor the reaction progress with a TLC board to ensure that the reaction is complete . Add 80ml of distilled water and stir for 2h, a lot of solids precipitate out. Discard the water layer until the solid precipitates and the water becomes clear, wash the precipitate with water until it is neutral, add 80 mL of ethyl acetate to dissolve, pass through a silica gel column, and elute with acetone:petroleum ether (3:2), collect the eluate and spin evaporate, and wash with chloroform / Methanol was recrystallized with a yield of 58.2%.
[0031] Colorless crystals, m.p.194.5-195.1°C (literature value: 195-196°C). IR(KBr), v, cm -1 : 2946.2, 1776.3, 1264.6, 1199.82. 1HNMR (DMSO, 600MHz), δ: 7.86(m, 1H, 2'-H); 7.8...
Embodiment 2
[0033] Synthesis of Quercetin Pentapropionate (2)
[0034] Weigh 610mg (1mmol) of rutin, add 5ml of propionic anhydride, stir with a magnetic stirrer for 0.5h, make it fully dissolved, add 5 drops of concentrated sulfuric acid, control the temperature at 65°C, reflux for 6h, monitor the reaction process with a TLC board to ensure that the reaction is complete . Add 80ml of distilled water and stir for 2h, a lot of solids precipitate out. Discard the water layer until the solid precipitates and the water becomes clear, wash the precipitate with water until it becomes neutral, add 80 mL of ethyl acetate to dissolve, pass through a silica gel column, and elute with acetone:petroleum ether (3:2), collect the eluate and spin evaporate, and wash with chloroform / Methanol was recrystallized with a yield of 57.3%, m.p.136.1-138.4°C. IR(KBr), v, cm -1 : 2936, 1769.2, 1244.6, 1108.8. 1 HNMR (CDCl 3 , 600MHz), δ: 7.86(m, 1H, 2′-H); 7.64(m, 1H, 6′-H); 7.60(s, 1H, 5′H); 7.54(s, 1H, 8H...
Embodiment 3
[0036] Synthesis of Quercetin Pentabenzoate (3)
[0037] Weigh 610mg (1mmol) of rutin, dissolve it in 20ml of dimethylformamide (DMF), add 5ml of benzoyl chloride, stir with a magnetic stirrer for 0.5h, make it fully dissolved, add 10 drops of piperidine, control the temperature Reflux at 65°C for 6h, and monitor the progress of the reaction with a TLC plate to ensure the completion of the reaction. Add 80ml of distilled water and stir for 2h, a lot of solids precipitate out. Discard the water layer until the solid precipitates and the water becomes clear, wash the precipitate with water until it becomes neutral, add 80 mL of ethyl acetate to dissolve, pass through a silica gel column, and elute with acetone:petroleum ether (3:2), collect the eluate and spin evaporate, and wash with chloroform / Methanol was recrystallized with a yield of 57.3%, m.p.112.3-1114.5°C. IR(KBr), v, cm -1 : 3406.0, 2926.1, 1745.3, 1259.6, 1129.8. 1 HNMR (CDCl 3 , 600MHz), δ: 7.78(m, 1H, 2′-H); 7...
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