Synthetic method of dihydrobenzofuran compound with chiral quaternary carbon center
A compound and carbon-centered technology, applied in organic chemistry methods, organic chemistry, etc., can solve problems such as the inability to obtain high optical purity 3-methyl-3-propargylchroman compounds
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Embodiment 1
[0029] Embodiment 1 (R It is hydrogen, R Substituted phenyl is phenyl ( ), R2 is 4-n-propylphenyl)
[0030] Under the protection of nitrogen, add palladium acetate (20 mg, 0.09 mmol), (S)-SEGPHOS (114 mg, 0.19 mmol), N,N-dimethylformamide (4 mL) into the reaction flask, and heat to 40 ° C for reaction 10 minutes. Continue to add 1-iodo-2-((2-methallyl)oxy)benzene ( ) (250 mg, 0.91 mmol), 4-n-propylphenylacetylene (263 mg, 1.82 mmol), sodium acetate (374 mg, 4.56 mmol) and N,N-dimethylformamide (4 mL), vacuum / nitrogen Replaced three times, heated to 100°C for 15 hours. After the reaction, the reaction solution was cooled to room temperature. Water (5 mL) was added to the reaction solution, and extracted with methyl tert-butyl ether (10 mL×2). The organic phases were combined, washed with water (15 ml × 3), dried over anhydrous sodium sulfate, concentrated by filtration, prepared on a silica gel plate (petroleum ether: ethyl acetate = 100:1) and purified to obtain (2) pro...
Embodiment 2
[0033] Embodiment 2 (R1 is hydrogen, and R1 substituted phenyl is phenyl ( ), R2 is 4-methylphenyl)
[0034] Under the protection of nitrogen, add palladium acetate (20 mg, 0.09 mmol), (S)-SEGPHOS (114 mg, 0.19 mmol), N,N-dimethylformamide (4 mL) into the reaction flask, and heat to 40 ° C for reaction 10 minutes. Continue to add 1-iodo-2-((2-methallyl)oxy)benzene ( ) (250 mg, 0.91 mmol), 4-methylphenylacetylene (212 mg, 1.83 mmol), sodium acetate (374 mg, 4.56 mmol), and N,N-dimethylformamide (4 mL), vacuum / nitrogen Replaced three times, heated to 100°C for 15 hours. After the reaction, the reaction solution was cooled to room temperature. Water (5 mL) was added to the reaction solution, and extracted with methyl tert-butyl ether (10 mL×2). The organic phases were combined, washed with water (15 ml × 3), dried over anhydrous sodium sulfate, concentrated by filtration, prepared on a silica gel plate (petroleum ether: ethyl acetate = 100:1) and purified to obtain (3) pro...
Embodiment 3
[0037] Embodiment 3 (R1 is hydrogen, and R1 substituted phenyl is phenyl ( ), R2 is hydroxyethyl)
[0038] Under nitrogen protection, add palladium acetate (20 mg, 0.09 mmol), (S)-SEGPHOS (84 mg, 0.14 mmol), N,N-dimethylformamide (3 mL) into the reaction flask, and heat to 40°C for reaction 10 minutes. Continue to add 1-iodo-2-((2-methallyl)oxy)benzene ( ) (250 mg, 0.91 mmol), 3-butyn-1-ol (128 mg, 1.83 mmol), sodium acetate (374 mg, 4.56 mmol), tetraethylammonium chloride (344 mg, 1.10 mmol) and N , N-dimethylformamide (3 mL), vacuum / nitrogen replacement three times, heated to 100°C for 15 hours. After the reaction, the reaction solution was cooled to room temperature. Water (5 mL) was added to the reaction solution, and extracted with methyl tert-butyl ether (10 mL×2). The organic phases were combined, washed with water (15 mL×3), dried over anhydrous sodium sulfate, filtered and concentrated. Preparation of silica gel plate (petroleum ether: ethyl acetate = 5:1) and...
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