反応 #470407

反応方程式

title compound

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

triphenylphosphine

triethylsilane

→

title product

収率 70.2%

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

収率 70.2%

溶媒

DMF

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   その他quenched with water
3. 3
   抽出extracted with 20% ethyl acetate in hexane
4. 4
   洗浄The organic layer was washed with brine
5. 5
   乾燥dried with Na2SO4
6. 6
   濃縮concentrated
7. 7
   その他the residue was purified by column chromatography on silica gel

実験手順

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).

出典