Reaktion #736209

Reaktionsgleichung

ethyl azodicarboxylate

2-cyano-pyrrol

triphenylphosphine

propargyl alcohol

→

1-(2-propynyl)-1H-pyrrole-2-carbonitrile

Ausbeute 46.7%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled at +5° C.
2. 2
   workup.WAITover half an hour at 0° to 5° C.
3. 3
   Temperaturwas maintained for 18 hours
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Filtrationfiltered
6. 6
   EinengenAfter concentrating the filtrate
7. 7
   Sonstigean oil was obtained which
8. 8
   Sonstigewas chromatographed over silica
9. 9
   WaschenElution with a hexane-ethyl acetate (7-3) mixture

Vorschrift

51.57 g of 2-cyano-pyrrol[prepared by the process of Can. J. Chem. Vol. 59, p. 2763 (1981)], 146.9 g of triphenylphosphine, and 43.95 g of propargyl alcohol were mixed together and 420 ml of tetrahydrofuran were added. The mixture was cooled at +5° C., and over half an hour at 0° to 5° C., 97.5 g of ethyl azodicarboxylate were introduced. The temperature was allowed to return to ambient, and stirring was maintained for 18 hours. The solvent was evaporated under reduced pressure, and the crystallized residue was taken up in ethyl ether and filtered. After concentrating the filtrate, an oil was obtained which was chromatographed over silica. Elution with a hexane-ethyl acetate (7-3) mixture yielded 34 g of 1-(2-propynyl)-1H-pyrrole-2-carbonitrile.

Quelle