반응 #940063

반응 방정식

N-(3-[1,3]Dioxolan-2-yl-phenyl)-acetamide

pyridinium-p-toluenesulfonate

→

N-(3-Formyl-phenyl)-acetamide

수율 99.0%

용매

acetone water

반응 조건

후처리

1. 1
   온도was refluxed for 1 hr
2. 2
   기타the bulk of the solvent (˜90%) removed under reduced pressure
3. 3
   추출The remaining solution was then extracted with EtOAc
4. 4
   세척the combined extracts washed with saturated NaHCO3, brine
5. 5
   건조dried with MgSO4
6. 6
   기타Evaporation of the solvent

실험 절차

A mixture of N-(3-[1,3]Dioxolan-2-yl-phenyl)-acetamide (7.8 g, 0.037 mol) and pyridinium-p-toluenesulfonate (2.8 g, 0.011 mol) in acetone-water (4:1, 400 mL) was refluxed for 1 hr. The solution was then cooled to room temperature, and the bulk of the solvent (˜90%) removed under reduced pressure. The remaining solution was then extracted with EtOAc, and the combined extracts washed with saturated NaHCO3, brine, and dried with MgSO4. Evaporation of the solvent gave N-(3-Formyl-phenyl)-acetamide (5.98 g, 98%) as an orange oil. 1H NMR (CDCl3) δ 2.22 (s, 3H), 7.46 (t, J=8 Hz, 1H), 7.59 (d, J=8 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 8.07 (s, 1H), 8.69 (br s, 1H), 9.94 (s, 1H). 13C NMR (CDCl3) δ 193.9, 171.0, 140.8, 138.5, 131.2, 127.5, 127.1, 122.0, 26.0.

출처