반응 #470407

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title compound

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

triphenylphosphine

triethylsilane

→

title product

수율 70.2%

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

수율 70.2%

용매

DMF

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후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   기타quenched with water
3. 3
   추출extracted with 20% ethyl acetate in hexane
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried with Na2SO4
6. 6
   농축concentrated
7. 7
   기타the residue was purified by column chromatography on silica gel

실험 절차

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).

출처