反应详情

2.0 g (0.0075 mol) of 2,6-dibromo-4-methoxy pyridine was dissolved in about 30 ml of diethyl ether. While cooling the solution in a dry ice-acetone bath in an argon atmosphere, 6.0 ml of a 1.6M-hexane solution of BuLi (0.0075×1.3 mol) was added thereto, followed by stirring the solution for about 10 minutes. After 2.0 g (0.0075×2.0 mol) of 4-methyl phenyl isocyanate dissolved in about 5 ml of diethyl ether was added to the reaction solution, the solution was removed from the bath and stirred at room temperature for about 40 minutes. The reaction solution was mixed with about 10 ml of a 1.2N-aqueous hydrochloric acid solution, and then distributed in ethyl acetate-saturated sodium bicarbonate water, followed by washing with saturated brine. The organic phase of the obtained solution was dried with anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluting solution: ethyl acetate/hexane) to separate a main fraction therefrom. The fraction was concentrated and then precipitated with hexane, thereby obtaining an aimed product.

1. additionwas added
2. additionwas added to the reaction solution
3. customthe solution was removed from the bath
4. stirringstirred at room temperature for about 40 minutes
5. additionThe reaction solution was mixed with about 10 ml of a 1.2N-aqueous hydrochloric acid solution
6. washby washing with saturated brine
7. dry with materialThe organic phase of the obtained solution was dried with anhydrous sodium sulfate
8. concentrationconcentrated
9. washsubjected to silica gel column chromatography (eluting solution: ethyl acetate/hexane)
10. customto separate a main fraction
11. concentrationThe fraction was concentrated
12. customprecipitated with hexane