تفاعل #45638

معادلة التفاعل

sodium hydrogencarbonate

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

2-furoyl chloride

pyridinium paratoluenesulfonate

→

compound

المردود 31.0%

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

المردود 31.0%

المذيبات

ethyl acetate

xylene

triethylamine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   أخرىThis reaction liquid
3. 3
   أخرىThe aqueous layer was separated
4. 4
   استخلاصthis was extracted twice with ethyl acetate
5. 5
   غسيلthis was washed with saturated brine
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   أخرىThe insoluble matter was separated by filtration
8. 8
   أخرىthe solvent was evaporated away
9. 9
   أخرىthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

الإجراء التجريبي

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.

المصدر