반응 #45638

반응 방정식

sodium hydrogencarbonate

4-Amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile

2-furoyl chloride

pyridinium paratoluenesulfonate

→

compound

수율 31.0%

7-Fluoro-2-(furan-2-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

수율 31.0%

용매

ethyl acetate

xylene

triethylamine

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   기타This reaction liquid
3. 3
   기타The aqueous layer was separated
4. 4
   추출this was extracted twice with ethyl acetate
5. 5
   세척this was washed with saturated brine
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   기타The insoluble matter was separated by filtration
8. 8
   기타the solvent was evaporated away
9. 9
   기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

실험 절차

4-Amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (100 mg, 0.41 mmol) was dissolved in xylene (10 ml), then at room temperature, triethylamine (70 μl), 2-furoyl chloride (49 μl, 0.50 mmol), pyridinium paratoluenesulfonate (31 mg, 0.12 mmol) were added. Next, this mixture liquid was stirred at 145° C. for 108 hours, then cooled to room temperature. This reaction liquid was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was separated, and this was extracted twice with ethyl acetate. The organic layers were combined, this was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1), and the entitled compound (40 mg, 31%) was obtained as a white solid.

출처