반응 #42750

반응 방정식

N-[3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-4-oxo-4H-chromen-7-yl]formamide

cesium carbonate

1,3-dibromopropane

→

title compound

3-(4-Chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도The mixture is cooled to room temperature
2. 2
   여과filtered through Celite
3. 3
   여과filter aid
4. 4
   세척The pad of Celite is washed with ethyl acetate and methylene chloride
5. 5
   기타the combined filtrates are evaporated in vacuo
6. 6
   기타to afford a brown solid
7. 7
   기타This is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1)

실험 절차

A stirred mixture of N-[3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-4-oxo-4H-chromen-7-yl]formamide (0.122 g, 0.34 mmol), cesium carbonate (0.444 g, 1.36 mmol, 4 eq.) and 1,3-dibromopropane (0.069 g, 0.34 mmol) in anhydrous N,N-dimethylformamide (3 ml) is heated at 60° C. under a nitrogen atmosphere for 2 h. The mixture is cooled to room temperature and filtered through Celite filter aid. The pad of Celite is washed with ethyl acetate and methylene chloride, and the combined filtrates are evaporated in vacuo to afford a brown solid. This is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1) to furnish the title compound as a yellow solid.

출처