반응 #76441

반응 방정식

methyl(3-heptafluorobutyramido-4-hydroxyphenyl)acetate

para-toluenesulfonic acid

→

methyl(2-heptafluoropropylbenzoxazol-5-yl)acetate

수율 67.8%

용매

toluene

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux (a Dean & Stark™
3. 3
   기타assembly was fitted
4. 4
   기타to remove water) for 24 hours
5. 5
   workup.ADDITIONthe mixture was diluted with ethyl acetate (150 ml)
6. 6
   세척The mixture was washed with saturated aqueous sodium bicarbonate solution and brine
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   기타the filtrate was evaporated in vacuo
10. 10
    기타The residue was purified by column chromatography on silica gel
11. 11
    세척eluting with dichloromethane

실험 절차

A mixture of methyl(3-heptafluorobutyramido-4-hydroxyphenyl)acetate (20.0 g, 0.053 mol) and para-toluenesulfonic acid (1.71 g) in toluene (150 ml) was heated at reflux (a Dean & Stark™ assembly was fitted to remove water) for 24 hours. The mixture was cooled to room temperature and the mixture was diluted with ethyl acetate (150 ml). The mixture was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane to give methyl(2-heptafluoropropylbenzoxazol-5-yl)acetate (12.9 g) as an off-white solid.

출처