反応 #42750

反応方程式

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

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   温度The mixture is cooled to room temperature
2. 2
   ろ過filtered through Celite
3. 3
   ろ過filter aid
4. 4
   洗浄The pad of Celite is washed with ethyl acetate and methylene chloride
5. 5
   その他the combined filtrates are evaporated in vacuo
6. 6
   その他to afford a brown solid
7. 7
   その他This is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1)

実験手順

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.

出典