تفاعل #42750

معادلة التفاعل

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

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is cooled to room temperature
2. 2
   ترشيحfiltered through Celite
3. 3
   ترشيحfilter aid
4. 4
   غسيلThe pad of Celite is washed with ethyl acetate and methylene chloride
5. 5
   أخرىthe combined filtrates are evaporated in vacuo
6. 6
   أخرىto afford a brown solid
7. 7
   أخرىThis is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:1)

الإجراء التجريبي

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.

المصدر