Reaction #470407

Reaction equation

title compound

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

triphenylphosphine

triethylsilane

→

title product

Yield 70.2%

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

Yield 70.2%

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to room temperature
2. 2
   Otherquenched with water
3. 3
   Extractionextracted with 20% ethyl acetate in hexane
4. 4
   WashThe organic layer was washed with brine
5. 5
   Dryingdried with Na2SO4
6. 6
   Concentrationconcentrated
7. 7
   Otherthe residue was purified by column chromatography on silica gel

Procedure

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