Réaction #42750

Équation de réaction

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

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture is cooled to room temperature
2. 2
   Filtrationfiltered through Celite
3. 3
   Filtrationfilter aid
4. 4
   LavageThe pad of Celite is washed with ethyl acetate and methylene chloride
5. 5
   Autrethe combined filtrates are evaporated in vacuo
6. 6
   Autreto afford a brown solid
7. 7
   AutreThis is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1)

Mode opératoire

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.

Source