反応 #52656

反応方程式

hydrochloric acid

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

5-chloro-2-oxindole

pyrrolidine

→

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

収率 10.2%

溶媒

ethanol

反応条件

後処理

1. 1
   ろ過the solid which remained were filtered
2. 2
   洗浄washed with more water (50 ml)
3. 3
   workup.DISSOLUTIONThe solid was then dissolved in ethyl acetate (200 ml)
4. 4
   乾燥the solution dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The solid which remained 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, 1.26 mmol), 5-chloro-2-oxindole (0.21 g, 1.26 mmol) and pyrrolidine (0.5 ml, 6.3 mmol) in ethanol (2 ml) was held in sealed tube at 100° C. for 12 hours. The mixture was then poured into 1N hydrochloric acid (100 ml) and the solid which remained were filtered and washed with more water (50 ml). The solid was then dissolved in ethyl acetate (200 ml), the solution dried over magnesium sulfate, filtered and then concentrated. The solid which remained was chromatographed (silica, 4/4/1 dichloromethane/hexanes/methanol) to give 60 mg (10%) of 5-chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one as a brownish-orange solid.

出典