Hydrochloric Acid → 3H-1,2-dihydro-1-pyrrolizinone

Reaktionsgleichung

[C:1]([CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1)#N.Cl.CC[O:13]CC>>[C:1]1(=[O:13])[C:9]2[N:5]([CH:6]=[CH:7][CH:8]=2)[CH2:4][CH2:3]1

Komponenten

Edukt 3

HCID 313Hydrochloric Acid

HCID 3283Diethyl Ether

HCID 965273-(Pyrrol-1-yl)propiononitrile

Produkt 1

HCID 973473H-1,2-dihydro-1-pyrrolizinoneAusbeute 65 %

Versuchsvorschrift

To a solution of 10 g N-cyanoethylpyrrole in 100 ml ether was added 2.5 g ZnCI2. Dried HCl was passed into the mixture at 5°-10° C. After 2 hours, the reaction mixture was allowed to stand at room temperature for 4 hours. Removed the solvent by suction, 20%. Aqueous NaOH was added until pH 3. The mixture was stirred at 80°-90° C. for 2 hours. Extracted with methylene chloride, dried over Na2SO4, evaporated the solvent, 8 g yellow solid was obtained. The crude product was crystallized from petroleum ether, 6.5 g compound (1) was obtained, as white crystals, mp 53°-54.5° C., yield 65%.