Reacción #162953

Ecuación de reacción

N-hydroxy-4-nitro-benzimidoyl chloride

phenyl propionic acid ethyl ester

3-(4-nitro-phenyl)-isoxazol-5-carboxylic acid ethyl ester

→

title compound

3-(4-Nitro-phenyl)-5-phenyl-isoxazole-4-carboxylic acid ethyl ester

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was refluxed for 16 hours instead
2. 2
   OtroThe crude product was purified by flash chromatography over silica gel with 10-30% EtOAc in light petroleum

Procedimiento

The title compound was prepared from N-hydroxy-4-nitro-benzimidoyl chloride and phenyl propionic acid ethyl ester by the same procedure as described for the synthesis of 3-(4-nitro-phenyl)-isoxazol-5-carboxylic acid ethyl ester in Example 1. The reaction mixture was refluxed for 16 hours instead of heating at 80° C. for 2.5 hours. The crude product was purified by flash chromatography over silica gel with 10-30% EtOAc in light petroleum to give the title compound in 40% yield. 1H NMR (DMSO-d6) δ: 0.98 (t, 3H), 4.11 (q, 2H), 7.53-7.61 (m, 3H), 7.87-7.93 (m, 4H), 8.32 (d, 2H); Mass (ES+), 339 (M++1).

Fuente