Reacción #1539633

Ecuación de reacción

HCl

potassium cyanide

4-(2,2′-dicyanoethenyl)styrene

ethanol

→

4-(1,2,2′-tricyanoethyl)styrene

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe mixture was concentrated under vacuum
2. 2
   workup.ADDITIONTen milliliters (10 mL) water was added to the residue
3. 3
   Extracciónthe mixture was extracted with ethyl acetate
4. 4
   ConcentraciónThe combined organic layers were concentrated under vacuum
5. 5
   Otrothe product was purified by column chromatography on silica gel using 20% ethyl acetate in hexane
6. 6
   OtroThe product recovered from the separation
7. 7
   workup.ADDITIONwas mixed with 1.5 mL methylene chloride and 10 mL hexane
8. 8
   Filtraciónfiltered
9. 9
   OtroA white solid was obtained (1.009 g, 44%)

Procedimiento

To a mixture of 2.00 g 4-(2,2′-dicyanoethenyl)styrene (11 mmol) and 30 mL ethanol was added a solution of 1.45 g potassium cyanide (22 mmol) in 3 mL water. The mixture was stirred at room temperature for 17 hours. 1.8 mL concentrated HCl (22 mmol) was then added and the mixture was concentrated under vacuum. Ten milliliters (10 mL) water was added to the residue, and the mixture was extracted with ethyl acetate. The combined organic layers were concentrated under vacuum, and the product was purified by column chromatography on silica gel using 20% ethyl acetate in hexane. The product recovered from the separation was mixed with 1.5 mL methylene chloride and 10 mL hexane, then filtered. A white solid was obtained (1.009 g, 44%).

Fuente