Réaction #470407

Équation de réaction

title compound

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

triphenylphosphine

triethylsilane

→

title product

Rendement 70.2%

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

Rendement 70.2%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   Autrequenched with water
3. 3
   Extractionextracted with 20% ethyl acetate in hexane
4. 4
   LavageThe organic layer was washed with brine
5. 5
   Séchagedried with Na2SO4
6. 6
   Concentrationconcentrated
7. 7
   Autrethe residue was purified by column chromatography on silica gel

Mode opératoire

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).

Source