Реакция #45895

Уравнение реакции

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

triethylamine

allyl alcohol

→

compound

Выход 32.5%

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

Выход 32.5%

Растворители

dimethylformamide

Условия реакции

Обработка

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

Методика

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.

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