反应详情

8.0 g 5-Bromomethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester were dissolved in 50 ml dry dimethylformamide. 7.8 g Silver trifluoroacetate were added and the mixture was stirred at room temperature for two hours. 30 ml brine were added and the mixture was stirred for two hours. The reaction mixture was filtered through a pad of celite, the solvent removed in vacuo and the resulting residue dissolved in 200 ml ethanol. The mixture was heated to reflux for three hours. Then the solvent was removed in vacuo and the residue dissolved in water and extracted five times with ethyl acetate. The combined organic layers were dried over MgSO4, the solvent removed in vacuo and the residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=2:3=>ethylacetate) to obtain 4.8 g 5-hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester as a solid.

1. stirringthe mixture was stirred for two hours
2. filtrationThe reaction mixture was filtered through a pad of celite
3. customthe solvent removed in vacuo
4. dissolutionthe resulting residue dissolved in 200 ml ethanol
5. temperatureThe mixture was heated
6. temperatureto reflux for three hours
7. customThen the solvent was removed in vacuo
8. dissolutionthe residue dissolved in water
9. extractionextracted five times with ethyl acetate
10. dry with materialThe combined organic layers were dried over MgSO4
11. customthe solvent removed in vacuo
12. customthe residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=2:3=>ethylacetate)