Method for synthesizing substituted furan
A furan and disubstitution technology, which is applied in the field of synthetic substituted furans, can solve the problems of complex post-processing, increased production costs, and limited prospects for industrial production, and achieves the effects of easy separation and purification, high yield, and easy availability of raw materials and reagents
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Embodiment 1
[0013] Add dichloroditriphenylpalladium phosphide (14mg, 0.02mmol), cuprous iodide (1.9mg, 0.01mmol), triethylamine (2ml), iodobenzene (204mg, 1mmol) into a dry reaction flask , 3-butyn-1-ol (84mg, 1.2mmol), reacted at 50°C for 3 hours, quenched the reaction with a 1:1 mixed solution of ethyl acetate and water, stirred for 0.5 hours, extracted the aqueous layer with ether, The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, spin-dried, and subjected to flash column chromatography (mobile phase: petroleum ether / ethyl acetate = 10:1) to obtain the intermediate product 4-phenyl- 3-butyn-1-ol 134mg, yield 92%. Add 5ml of dichloroethane and Dess-Martin Periodinane (318mg, 0.75mmol) to 73mg (0.5mmol) of 4-phenyl-3-butyn-1-ol, under nitrogen protection at room temperature, stir for 1 hour, saturated bicarbonate The reaction was quenched by sodium, extracted three times with ether, the organic phase was washed with saturated b...
Embodiment 2
[0017] Add dichloroditriphenylpalladium phosphide (35mg, 0.01mmol), cuprous iodide (4.8mg, 0.025mmol), triethylamine (10ml), iodobenzene (510mg, 2.5mmol) into a dry reaction flask ), 4-pentyn-2-ol (252mg, 3mmol), reacted at 45°C for 40 minutes, quenched the reaction with a 1:1 mixed solution of ethyl acetate and water, stirred for 0.5 hours, extracted the aqueous layer with ether, The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, spin-dried, and subjected to flash column chromatography (mobile phase: n-hexane / ethyl acetate = 10:1) to obtain the light yellow oily product 5-benzene Amyl-4-pentyn-2-ol 390 mg (97.5%). Add 10ml of dichloroethane and Dess-MartinPeriodinane (1.48g, 3.5mmol) to 390mg (2.5mmol) of the obtained intermediate product 5-phenyl-4-pentyn-2-ol, and react under nitrogen protection at room temperature for 2.5 hours , TLC detected that the reaction was complete, the reaction was quenched by saturated s...
Embodiment 3
[0020]Add dichloroditriphenylpalladium phosphide (35mg, 0.01mmol), cuprous iodide (4.8mg, 0.025mmol), triethylamine (10ml), 4-methoxy iodobenzene to a dry reaction flask (585mg, 2.5mmol), 4-pentyn-2-ol (252mg, 3mmol), react at 70°C for 40 minutes, quench the reaction with a 1:1 mixed solution of ethyl acetate and water, stir for 0.5 hours, water The layers were extracted with ether, the combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, spin-dried, flash column chromatography (mobile phase: petroleum ether / ethyl acetate = 6:1), and a colorless The oily product 5-(4-methoxy)phenyl-4-pentyn-2-ol was 435mg, and the yield was 91.6%. Add 10ml of dichloroethane and Dess-MartinPeriodinane (1.27g, 3mmol) to 380mg (2.0 mmol) of the product, under nitrogen protection at 80°C, stir for 4 hours, quench the reaction with saturated sodium bicarbonate, extract 3 times with ether, and The organic phase was washed with brine, dried over an...
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