Efficient and selective synthesis method of 2-hydroxyphenyl styryl ether compounds
A technology of hydroxyphenyl styryl ether and hydroxyphenyl styrene, which is applied in the field of biosynthesis, can solve the problems of not wide range of reaction applications, low reaction efficiency, many reaction steps, etc., and achieves controllable chemical selectivity, chemical The effect of high selectivity and mild synthesis conditions
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Embodiment 1
[0031] Embodiment 1: Preparation of 3a product
[0032] In a 25 mL round bottom flask at room temperature, add 3 mmol, 282 mg phenol and 3.6 mmol, 828 mg iodovinylbenzene, 0.1 equiv, 48.6 mg FeCl 3 , 0.2 equiv, 130mg enaminone ligand, 2 equiv, 978mg cesium carbonate, reacted in dimethyl sulfoxide 10mL solvent at 80°C for 5 hours, after the reaction was completed and cooled, add 10mL saturated NaCl aqueous solution to the system, and use acetic acid Ethyl ester was extracted 3 times, 10 mL each time, the organic phases were combined and washed with anhydrous Na 2 SO 4 After drying, the solvent was distilled off, and 540 mg of the 2-hydroxyphenyl styryl ether was obtained by 200-300 mesh silica gel column chromatography, with a yield of 85%. H NMR spectrum see figure 1 .
[0033] colorless oily liquid;
[0034] 1 H-NMR (500 MHz, d 6 -DMSO): δ 9.98 (s, 1 H), 7.46-7.45 (d, J = 7.5 Hz, 2H), 7.33-7.27 (m, 4H), 7.24-7.22 (d, J = 7.5 Hz, 1 H), 7.13-7.09 (m, 2 H),6.90-6.89 (...
Embodiment 2
[0037] Embodiment 2: Preparation of 3b product
[0038] In a 25 mL round bottom flask at room temperature, add 3 mmol, 384 mg 4-chlorophenol and 3.6 mmol, 828 mg iodovinylbenzene, 0.1 equiv, 48.6 mg FeCl 3 , 0.2 equiv, 130 mg enaminone ligand, 2 equiv, 978 mg cesium carbonate, in dimethyl sulfoxide 10 mL solvent 80 o C under the condition of reaction for 5 hours, after the reaction is completed and cooled, add 10 mL of saturated NaCl aqueous solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, and wash with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated, and 200-300 mesh silica gel column chromatography was used to obtain 667 mg of the 2-hydroxy(3-chloro)phenyl styryl ether, with a yield of 90%. H NMR spectrum see figure 2 .
[0039] colorless oily liquid;
[0040] 1 H-NMR (500 MHz, d 6 -DMSO): δ 10.58 (s, 1 H), 7.48-7.46 (d, J = 7.5 Hz, 2H), 7.33-7.23 (m, 4H), 7.11-7.08 (d, J = 15.5 Hz, 1 H), 6.92-...
Embodiment 3
[0043] Embodiment 3: the preparation of 3c product
[0044] In a 25 mL round bottom flask at room temperature, add 3 mmol, 384 mg 3-chlorophenol and 3.6 mmol, 828 mg iodovinylbenzene, 0.1 equiv, 48.6 mg FeCl 3 , 0.2 equiv, 130mg enaminone ligand, 2 equiv, 978mg cesium carbonate, in dimethyl sulfoxide 10mL solvent 80 o C under the condition of reaction for 5 hours, after the reaction is completed and cooled, add 10 mL of saturated NaCl aqueous solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, and wash with anhydrous NaCl 2 SO 4 After drying, the solvent was distilled off, and 200-300 mesh silica gel column chromatography gave 704 mg of the 2-hydroxy(4-chloro)phenyl styryl ether, with a yield of 95%. H NMR spectrum see image 3 .
[0045] yellow oily liquid;
[0046] 1 H-NMR (500 MHz, d 6 -DMSO): δ 10.34 (s, 1 H), 7.54-7.52 (d, J = 8.0 Hz, 2H), 7.35-7.32 (m, 2H), 7.27-7.26 (d, J = 7.3 Hz, 1 H), 7.24-7.23 (d, J =...
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