反应详情

温度

-70 °C

BuLi (0.118 mol) was added dropwise at −70° C. under N2 flow to a solution of 4-phenyl-thiazole (0.097 mol) in THF (205 ml). The mixture was stirred at −70° C. for 1 hour. A solution of intermediate (13) (0.0692 mol) in THF (205 ml) was added dropwise. The mixture was stirred at −70° C. for 2 hours, brought to -30° C. over a 90-min period, poured out into NH4Cl 10% and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (39.5 g) was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc 80/20; 20–45 μm). The pure fractions were collected and the solvent was evaporated. A part (1.5 g) of the residue (18 g, 62%) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 1.5 g (84%) of 3-(3-chlorophenyl)-α-(4-phenyl-2-thiazolyl)-2,1-benzisoxazole-5-methanol (intermediate 14), mp. 136° C.

1. stirringThe mixture was stirred at −70° C. for 2 hours
2. waitbrought to -30° C. over a 90-min period
3. extractionextracted with DCM
4. customThe organic layer was separated
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customthe solvent was evaporated
8. customThe residue (39.5 g) was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc 80/20; 20–45 μm)
9. customThe pure fractions were collected
10. customthe solvent was evaporated
11. customA part (1.5 g) of the residue (18 g, 62%) was crystallized from 2-propanone
12. filtrationThe precipitate was filtered off
13. customdried