تفاعل #45895

معادلة التفاعل

4-Cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl trifluoromethanesulfonate

triethylamine

allyl alcohol

→

compound

المردود 32.5%

2-Cyclopropyl-7-(1-hydroxymethylvinyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

المردود 32.5%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction liquid
2. 2
   تركيزwas concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   غسيلwashed with water and saturated brine
5. 5
   تجفيفAfter drying over anhydrous sodium sulfate
6. 6
   أخرىthe insoluble matter was separated by filtration
7. 7
   أخرىthe residue obtained by concentration
8. 8
   أخرىwas purified by silica gel column chromatography (eluent, n-hexane

الإجراء التجريبي

4-Cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl trifluoromethanesulfonate (I-323) (760 mg, 1.80 mmol) was dissolved in dimethylformamide (10 ml), then triethylamine (276 μl, 1.98 mmol), allyl alcohol (209 mg, 3.60 mmol), 1,1′-bis(diphenylphosphino)ferrocene (79.8 mg, 0.144 mmol) and palladium(II) acetate (24.2 mg, 0.108 mmol) were added, followed by stirring in an oil bath at 100° C. under argon atmosphere for 16 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1, v/v) to obtain the entitled compound (193 mg, 32%) as a colorless oily substance.

المصدر