反应详情

In tetrahydrofuran (100 ml), methyl 4-bromobenzoate (5.04 g) and diethyl-3-pyridylborane (Chem. Pharm. Bull., 33, 4755, 1985) (2.30 g) were dissolved, followed by the addition of tetrabutylammonium bromide (2.51 g), potassium hydroxide (2.63 g), tetrakis(triphenylphosphine)palladium (O) (1.8 g) and water (1 ml) under an argon atmosphere. The resulting mixture was heated under reflux for 2 hours. After ice cooling, an aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer so separated was dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent was purified by chromatography on a silica gel column (hexane: ethyl acetate=1:1). The solvent was then distilled off. To the residue, methanol and IN aqueous hydrochloric acid in ethanol were added. The solvent was distilled off again. Tetrahydrofuran was added to the residue and the solid so precipitated was collected by filtration. After drying, the title compound (1.76 g, 45%) was obtained as a colorless solid.

1. temperatureThe resulting mixture was heated
2. temperatureunder reflux for 2 hours
3. customThe organic layer so separated
4. dry with materialwas dried over anhydrous magnesium sulfate
5. customThe residue obtained
6. distillationby distilling off the solvent
7. customwas purified by chromatography on a silica gel column (hexane: ethyl acetate=1:1)
8. distillationThe solvent was then distilled off
9. additionTo the residue, methanol and IN aqueous hydrochloric acid in ethanol were added
10. distillationThe solvent was distilled off again
11. additionTetrahydrofuran was added to the residue
12. customthe solid so precipitated
13. filtrationwas collected by filtration
14. customAfter drying