反应详情

Thionyl chloride (1 mL) was added to (6-methyl-pyridin-3-yl)-methanol (300 mg, 2.44 mmol) at 0° C., and the solution was stirred at room temperature for 20 minutes. The reaction solution was partitioned in an aqueous solution of saturated sodium bicarbonate and ethyl acetate. This organic layer was separated, washed with brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo. N,N-dimethylformamide (5 mL), phenol (230 mg, 2.44 mmol) and potassium carbonate (674 mg, 4.88 mmol) were added to this residue at room temperature. This reaction mixture was stirred at room temperature for 40 minutes, then, further stirred for at 60° C. 40 minutes. The reaction solution was partitioned in water and ethyl acetate. The organic layer was separated, washed with water and brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (heptane/ethyl acetate=2/1), and the title compound (323 mg, 66%) was obtained as a white solid.

1. customThe reaction solution was partitioned in an aqueous solution of saturated sodium bicarbonate and ethyl acetate
2. customThis organic layer was separated
3. washwashed with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe organic layer was filtered
6. customthe solvent was evaporated in vacuo
7. stirringThis reaction mixture was stirred at room temperature for 40 minutes
8. stirringfurther stirred for at 60° C
9. custom40 minutes
10. customThe reaction solution was partitioned in water
11. customThe organic layer was separated
12. washwashed with water and brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationThe organic layer was filtered
15. customthe solvent was evaporated in vacuo
16. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate=2/1)