反应详情

温度

-70 °C

nBuLi 1.6 M in hexane (0.112 mol) was added dropwise at −70° C. under N2 flow to a mixture of 5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole (0.097 mol) in THF (300 ml). The mixture was stirred at −70° C. for 15 min. A mixture of 4-methylbenzaldehyde (0.112 mol) in THF (100 ml) was added dropwise. The mixture was stirred at −70° C. for 30 min, then hydrolized and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue was purified by column chromatography over silica gel (20-45 μm) (eluent: DCM/EtOAc 96/4). The pure fractions were collected and the solvent was evaporated, yielding 13 g (38.3%) of 3-(3-chlorophenyl)-α-(4-methylphenyl)-2,1-benzisoxazole-5-methanol (intermediate 18).

1. additionwas added dropwise
2. stirringThe mixture was stirred at −70° C. for 30 min
3. extractionhydrolized and extracted with EtOAc
4. customThe organic layer was separated
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customthe solvent was evaporated till dryness
8. customThe residue was purified by column chromatography over silica gel (20-45 μm) (eluent: DCM/EtOAc 96/4)
9. customThe pure fractions were collected
10. customthe solvent was evaporated