反应详情

To a solution of 2-methyl-5-phenoxymethyl-pyridine described in Preparation Example 186 (323 mg, 1.62 mmol) in methylene chloride was added 3-chloroperoxylbenzoic acid (473 mg, 1.78 mmol, 65%) at 0° C., and the solution was stirred at room temperature for 7 hours. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then partitioned with ethyl acetate. The organic layer was separated, washed with an aqueous solution of saturated sodium bicarbonate and brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo. Acetic anhydride (4 mL) was added to this residue, which was then stirred for 30 minutes at 120° C. This reaction solution was cooled to room temperature, then, the solvent was evaporated in vacuo. Ethanol (5 mL), and an aqueous solution of 5N sodium hydroxide (2 mL) were added to this residue, and the solution was stirred at room temperature for 45 minutes. This reaction solution was concentrated in vacuo, the residue was partitioned in water and ethyl acetate. The 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, the residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=1/1), and the title compound (167 mg, 48%) was obtained as a white solid.

1. customwhich was then partitioned with ethyl acetate
2. customThe organic layer was separated
3. washwashed with an aqueous solution of saturated sodium bicarbonate and brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe organic layer was filtered
6. customthe solvent was evaporated in vacuo
7. additionAcetic anhydride (4 mL) was added to this residue, which
8. stirringwas then stirred for 30 minutes at 120° C
9. temperatureThis reaction solution was cooled to room temperature
10. customthe solvent was evaporated in vacuo
11. additionEthanol (5 mL), and an aqueous solution of 5N sodium hydroxide (2 mL) were added to this residue
12. stirringthe solution was stirred at room temperature for 45 minutes
13. concentrationThis reaction solution was concentrated in vacuo
14. customthe residue was partitioned in water
15. customThe organic layer was separated
16. washwashed with brine
17. dry with materialdried over anhydrous magnesium sulfate
18. filtrationThe organic layer was filtered
19. customthe solvent was evaporated in vacuo
20. customthe residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=1/1)