反应详情

温度

90 °C

Trimethylaluminium (3 mL of a 2 M solution in toluene, 6 mmol) was added dropwise to a stirred solution of isopropylamine (355 mg, 6.0 mmol) in dioxane (4 mL) at room temperature and under argon. After 1 h, a solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (537 mg, 1.5 mmol) in dioxane (4 mL) was added and the reaction mixture warmed to 90° C. After 2 h the reaction mixture was cooled and poured onto ice/water. The resultant mixture was extracted with ethyl acetate then the combined extracts were washed with Seignette salt solution. The organic phase was dried, filtered and evaporated then purified by chromatography (silica, 0 to 60% ethyl acetate in heptane) then trituration with diisopropyl ether to give the title compound (76 mg, 15%) as a white solid. MS: m/e=332.4 [M+H]+.

1. temperatureAfter 2 h the reaction mixture was cooled
2. additionpoured onto ice/water
3. extractionThe resultant mixture was extracted with ethyl acetate
4. washthe combined extracts were washed with Seignette salt solution
5. customThe organic phase was dried
6. filtrationfiltered
7. customevaporated
8. customthen purified by chromatography (silica, 0 to 60% ethyl acetate in heptane)