反応 #52688

反応方程式

hydrochloric acid

3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

5-bromo-2-oxindole

pyrrolidine

→

5-bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one

収率 13.0%

溶媒

ethanol

反応条件

後処理

1. 1
   その他the solids removed by filtration
2. 2
   洗浄washed with more water (50 ml)
3. 3
   workup.DISSOLUTIONThe solids were then dissolved in ethyl acetate (200 ml)
4. 4
   洗浄the solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml)
5. 5
   乾燥dried with magnesium sulfate
6. 6
   濃縮concentrated
7. 7
   その他The crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol)

実験手順

A mixture of 3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde (0.4 g), 5-bromo-2-oxindole (0.27 g) and pyrrolidine (0.5 ml) in ethanol (2 ml) was held in a sealed tube at 100° C. for 12 hours. The mixture was then added to 1N hydrochloric acid (100 ml) and the solids removed by filtration and washed with more water (50 ml). The solids were then dissolved in ethyl acetate (200 ml), the solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml), dried with magnesium sulfate and concentrated. The crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol) to give 80 mg (13%) of 5-bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one as a reddish-brown solid.

出典