反应详情

温度

-78 °C

4-(t-Butyldimethylsilyloxy)-1-butyne (1.17 g, 6.4 mmol) was dissolved in dry tetrahydrofuran (20 ml) under argon atmosphere, which was then cooled down to −78° C. n-Butyllithium (2.29 ml, 5.72 mmol, 2.5M solution in tetrahydrofuran) was slowly added dropwise thereto, and the mixture was stirred at −78° C. for 30 minutes. To this mixture was added dropwise 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-one (1.14 g, 3.18 mmol) dissolved in dry tetrahydrofuran (10 ml) at −78° C., and the resulting reaction mixture was stirred at room temperature for 3 hours, and the reaction mixture was cooled to 0° C. The reaction was quenched with water, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (1.6 g, yield 93%) as a colorless oil.

1. additionwas slowly added dropwise
2. customthe resulting reaction mixture
3. stirringwas stirred at room temperature for 3 hours
4. temperaturethe reaction mixture was cooled to 0° C
5. customThe reaction was quenched with water
6. extractionthe reaction solution was extracted with ethyl acetate
7. washThe organic layer was washed with water and saturated sodium chloride solution
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated