تفاعل #45589

معادلة التفاعل

N-(5-cyano-2-fluoro-3,3′-dihydroxy-6-methylbiphenyl-4-yl)isobutylamide

p-toluenesulfonic acid monohydrate

toluene

→

compound

المردود 54.4%

7-Fluoro-6-(3-hydroxyphenyl)-2-isopropyl-5-methyl-1,3-benzoxazole-4-carbonitrile

المردود 54.4%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةunder reflux for 2.5 hours
3. 3
   درجة الحرارةAfter cooling
4. 4
   غسيلsuccessively washed with 1 N hydrochloric acid and saturated brine
5. 5
   تجفيفdried on anhydrous magnesium sulfate
6. 6
   أخرىthe solvent was evaporated away under reduced pressure
7. 7
   أخرىto obtain a pale brown residue
8. 8
   أخرىThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

الإجراء التجريبي

A mixture of N-(5-cyano-2-fluoro-3,3′-dihydroxy-6-methylbiphenyl-4-yl)isobutylamide (I-56) (60 mg, 0.183 mmol), p-toluenesulfonic acid monohydrate (10.4 mg, 0.0548 mmol) and toluene (5 ml) was heated under reflux for 2.5 hours. After cooling, this was diluted with ethyl acetate, successively washed with 1 N hydrochloric acid and saturated brine, dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (30.9 mg, 54%) as a pale yellow solid.

المصدر