Reaktion #343563

Reaktionsgleichung

potassium phthalimide

N-chlorosuccinimide

diphenyl diselenide

water

→

colorless crystals

N-2-(2-Furanyl)propenylphthalimide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3
2. 2
   workup.DISTILLATIONThe hexane was distilled off at atmospheric pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 200 ml of DMF
4. 4
   SonstigeAfter 45 min. the cooled reaction mixture
5. 5
   Filtrationthe precipitated product was filtered off
6. 6
   Sonstigerecrystallized from ethylacetate/2-propanol

Vorschrift

To a solution of 8.35 g (0.077 mole) of the olefin of Step A in 310 ml of DMF was added 12.37 g (0.093 mole) of N-chlorosuccinimide and 1.46 g (0.0047 mole) of diphenyl diselenide. After 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3. The hexane was distilled off at atmospheric pressure and the residue was dissolved in 200 ml of DMF, 9.49 g (0.051 mole) of potassium phthalimide was added and the mixture was warmed to 90° C. under N2. After 45 min. the cooled reaction mixture was poured into water and the precipitated product was filtered off and recrystallized from ethylacetate/2-propanol, affording 3.57 g colorless crystals, mp. 136°-137° C.

Quelle