Reacción #45862

Ecuación de reacción

magnesium chloride

Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonate

→

compound

Rendimiento 90.0%

Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate

Rendimiento 90.0%

Disolventes

water

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   OtroThe solvent was evaporated away under reduced pressure
3. 3
   OtroThe aqueous layer was separated
4. 4
   Extracciónextracted twice with ethyl acetate
5. 5
   Lavadowashed with saturated brine
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   OtroThe insoluble matter was separated by filtration
8. 8
   Otrothe solvent was evaporated away
9. 9
   Otrothe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Procedimiento

Dimethyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)malonate (I-294) (2.887 g, 7.11 mmol) was dissolved in dimethyl sulfoxide (50 ml) and water (5 ml), then at room temperature, magnesium chloride (2.03 g, 21.34 mmol) was added. The solution was stirred at 90° C. for 23 hours, then cooled to room temperature. The solvent was evaporated away under reduced pressure, the residue was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=3:1, v/v) to obtain the entitled compound (2.216 g, 90%) as a pale yellow solid.

Fuente