Preparation method of conjugated diene compound
A conjugated diene and compound technology, applied in the field of preparation of conjugated diene compounds, can solve the problems of expensive, excessive oxidant and the like
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Embodiment 1
[0014] Example 1: Compound (E)-2-phenyl-2-(4,4-bis(4-methoxyphenyl)-1,3-butadienyl)-1,3-dithiane preparation:
[0015] Into a 25 mL round-bottomed flask was added (Z)-2-(2-chloro-2-phenylethenyl)-1,3-dithiane (77 mg, 0.3 mmol), 1,1-dithiane (77 mg, 0.3 mmol) in turn (4-Methoxyphenyl)ethylene (48 mg, 0.2 mmol) and 6 mL of 1,2-dichloroethane were added with boron trifluoride ether (76 μL, 0.6 mmol) and stirred at room temperature , monitor the reaction by thin-layer chromatography, add 1 mol / ml aqueous sodium bicarbonate solution to the reaction system after the reaction to quench the reaction, and extract three times with dichloromethane (15 ml), combine the organic phases, and use saturated common salt for the organic phase. Washed with water (15 mL) three times, dried over anhydrous sodium sulfate, filtered, and volatiles were removed in a vacuum state, and the product was obtained by column chromatography in a yield of 69%.
[0016] In a 25 mL round-bottomed flask, add (Z)...
Embodiment 2
[0020] Example 2: Compound (E)-2-(4-methylphenyl)-2-(4,4-bis(4-methoxyphenyl)-1,3-butadienyl)-1, Preparation of 3-Dithiane:
[0021] In a 25 mL round-bottomed flask was sequentially added (Z)-2-(2-chloro-2-(4-methylphenyl)vinyl)-1,3-dithiane (81 mg, 0.3 mmol) , 1,1-bis(4-methoxyphenyl)ethylene (48 mg, 0.2 mmol) and 6 mL of 1,2-dichloroethane, boron trifluoride ether (76 μL, 0.6 mmol) was added ) was stirred at room temperature, and the reaction was monitored by thin-layer chromatography. After the reaction was completed, 1 mol / ml aqueous sodium bicarbonate solution was added to the reaction system to quench the reaction, and extracted three times with dichloromethane (15 ml), and the organic phases were combined. , the organic phase was washed three times with saturated brine (15 mL), dried over anhydrous sodium sulfate, filtered, and the volatiles were removed under vacuum, and the product was obtained by column chromatography with a yield of 72%.
[0022] The product obtai...
Embodiment 3
[0025] Example 3: Compound (E)-2-(4-methoxyphenyl)-2-(4,4-bis(4-methoxyphenyl)-1,3-butadienyl)-1 , the preparation of 3-dithiane:
[0026]In a 25 mL round-bottomed flask, sequentially add (Z)-2-(2-chloro-2-(4-methoxyphenyl)vinyl)-1,3-dithiane (86 mg, 0.3 mmol) ), 1,1-bis(4-methoxyphenyl)ethylene (48 mg, 0.2 mmol) and 6 mL of 1,2-dichloroethane, boron trifluoride ether (76 μL, 0.6 mmol) was added mol) at room temperature, and the reaction was monitored by thin-layer chromatography. After the reaction was completed, 1 mol / mL aqueous sodium bicarbonate solution was added to the reaction system to quench the reaction, and extracted with dichloromethane (15 mL) three times, and the organic The organic phase was washed three times with saturated brine (15 mL), dried over anhydrous sodium sulfate, filtered, and the volatiles were removed under vacuum, and the product was obtained by column chromatography with a yield of 76%.
[0027] The product obtained in Example 3 (E)-2-(4-metho...
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