反应详情

To a suspension of sodium hydride (170 mg, 4.24 mmol) in THF (7 mL) at 0° C. was added a solution of [3-butyl-5([E]-styryl)-isoxazol-4-yl]-methanol (993 mg, 3.86 mmol) in THF (17 mL) and the mixture was stirred for 30 min at room temperature. The reaction mixture was cooled to 5° C. and a solution of methyl 6-bromonicotinate (1.0 g, 4.6 mmol) in THF (17 mL) was added dropwise. The mixture was stirred at room temperature for 2 days, poured over ice and stirred for 5 min. The mixture was extracted twice with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated to a yellow oily solid. The crude material was purified by flash chromatography (silica gel, heptane:ethyl acetate 1:0 to 3:2) to afford the title compound (1.17 g, 77%) as an orange semisolid. MS: m/e=393.2 [M+H]+.

1. temperatureThe reaction mixture was cooled to 5° C.
2. stirringThe mixture was stirred at room temperature for 2 days
3. additionpoured over ice
4. stirringstirred for 5 min
5. extractionThe mixture was extracted twice with ethyl acetate
6. washwashed with brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated to a yellow oily solid
9. customThe crude material was purified by flash chromatography (silica gel, heptane:ethyl acetate 1:0 to 3:2)