反应详情

A mixture of tert-butyl({5-[(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl]-2-methylfuran-3-yl}methoxy)dimethylsilane (3.0 g), 1-bromo-4-[3-(methylsulfanyl)propoxy]benzene (2.8 g), tetrakis(triphenylphosphine)palladium(0) (0.5 g), 2N aqueous sodium carbonate solution (12 mL) and 1,2-dimethoxyethane (20 mL) was stirred overnight with refluxing under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (20 mL), 1N tetrabutylammonium fluoride in tetrahydrofuran (10 mL) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, purified by silica gel chromatography (0% ethyl acetate/hexane to 40% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (2.2 g, 84%) as a white crystal.

1. temperaturewith refluxing under an argon atmosphere
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. dissolutionThe residue was dissolved in tetrahydrofuran (20 mL)
7. addition1N tetrabutylammonium fluoride in tetrahydrofuran (10 mL) was added
8. stirringthe mixture was stirred at room temperature for 2 hr
9. additionThe reaction mixture was poured into water
10. extractionthe mixture was extracted with ethyl acetate
11. washThe organic layer was washed with saturated brine
12. dry with materialdried over magnesium sulfate
13. customThe solvent was evaporated under reduced pressure
14. custompurified by silica gel chromatography (0% ethyl acetate/hexane to 40% ethyl acetate/hexane)
15. customcrystallized from ethyl acetate/hexane