Ammonium Chloride → 3-(3-Chlorophenyl)-alpha-(4-phenyl-2-thiazolyl)-2,1-benzisoxazole-5-methanol

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Reaction Conditions

Reaction Steps

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.

Provenance & Evidence