Reacción #42750

Ecuación de reacción

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

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is cooled to room temperature
2. 2
   Filtraciónfiltered through Celite
3. 3
   Filtraciónfilter aid
4. 4
   LavadoThe pad of Celite is washed with ethyl acetate and methylene chloride
5. 5
   Otrothe combined filtrates are evaporated in vacuo
6. 6
   Otroto afford a brown solid
7. 7
   OtroThis is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1)

Procedimiento

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.

Fuente