Reacción #470407

Ecuación de reacción

title compound

2-pyridinyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

triphenylphosphine

triethylsilane

→

title product

Rendimiento 70.2%

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxaldehyde

Rendimiento 70.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Otroquenched with water
3. 3
   Extracciónextracted with 20% ethyl acetate in hexane
4. 4
   LavadoThe organic layer was washed with brine
5. 5
   Secadodried with Na2SO4
6. 6
   Concentraciónconcentrated
7. 7
   Otrothe residue was purified by column chromatography on silica gel

Procedimiento

To a stirred mixture of the title compound of Step A (690 mg, 1.30 mmol), palladium(II) acetate (9 mg, 0.04 mmol) and triphenylphosphine (31 mg, 0.12 mmol) in DMF (4 mL) was added triethylsilane (0.42 mL, 2.60 mmol). The resulting mixture was stirred at 60° C. for 5 h. The reaction mixture was cooled to room temperature, quenched with water, and extracted with 20% ethyl acetate in hexane. The organic layer was washed with brine, dried with Na2SO4 and concentrated, and the residue was purified by column chromatography on silica gel using hexane/EtOAc as eluent to provide the title product as a yellow solid (400 mg, 70% yield).

Fuente