反应详情

MeMgBr (3M in THF, 313 mL, 937.2 mmol) was added dropwise at 0° C. to 5-(3-chlorophenyl)isoxazole-3-carbaldehyde (177 g, 252 mmol) in THF (3 L). The mixture was allowed to attain room temperature, stirred at that temperature for 3 h and then quenched with aq. NH4Cl at 0° C. and the solvent was distilled off. To the remaining was added EtOAc and filtered through a plug of celite. The organic layer was washed with water, saturated brine and concentrated. The crude product was purified by flash column chromatography on silica using heptane/EtOAc=80:20, to give the title compound (70 g, 37%) as a white-yellow solid. 1H NMR: 7.73 (m, 1H), 7.63 (m, 1H), 7.38 (m, 2H), 6.57 (s, 1H), 5.07 (q, 1H), 2.44 (s, 1H), 1.59 (d, 3H).

1. customto attain room temperature
2. customquenched with aq. NH4Cl at 0° C.
3. distillationthe solvent was distilled off
4. additionTo the remaining was added EtOAc
5. filtrationfiltered through a plug of celite
6. washThe organic layer was washed with water, saturated brine
7. concentrationconcentrated
8. customThe crude product was purified by flash column chromatography on silica