Reaktion #53072

Reaktionsgleichung

benzoylchloride

diisopropylamine

n-butyl lithium

1-methyl-2-indolinone

→

1-methyl-3-(1-hydroxy-1-phenyl-methylidene)-2-indolinone

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 45 minutes at −70° C
2. 2
   workup.WAITThe reaction solution is left
3. 3
   Temperaturto heat up slowly within 14 hours
4. 4
   workup.ADDITIONIt is then poured onto sodium chloride solution
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   SonstigeThe combined organic extracts are dried
7. 7
   Einengenconcentrated by evaporation
8. 8
   SonstigeThe residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=200:8:1)

Vorschrift

4.15 g (41 mmol) of diisopropylamine are placed in 50 ml of THF, cooled to −70° C. and combined with a solution of 14.4 ml of (36 mmol) of n-butyl lithium solution (2.5 mol in toluene) and stirred for 10 minutes. Then a solution of 5.0 g (34 mmol) of 1-methyl-2-indolinone in 30 ml of THF is added dropwise and stirred for 45 minutes at −70° C. Then 5.8 g (0.041 mol) of benzoylchloride are added dropwise. The reaction solution is left to heat up slowly within 14 hours. It is then poured onto sodium chloride solution and extracted with ethyl acetate. The combined organic extracts are dried and concentrated by evaporation. The residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=200:8:1).

Quelle