Reacción #214169

Ecuación de reacción

glyoxylic acid

2-acetylfuran

→

title compound

Rendimiento 21.7%

4-(2-Furanyl)-4-oxo-2-butenoic acid

Rendimiento 21.7%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated at 125°-135° C. for about 5 hours
2. 2
   Otrothe water is removed as it
3. 3
   Otrocyrstallizes over about a 16 hour period
4. 4
   workup.DISSOLUTIONis dissolved in 600 cc of ethyl acetate
5. 5
   Extracciónextracted into 600 cc of 10% sodium carbonate
6. 6
   workup.ADDITIONThe aqueous solution is treated with activated charcoal
7. 7
   Filtracióna filter aid, and then filtered
8. 8
   Otrothe solid which precipitates
9. 9
   Extracciónis extracted with ethyl acetate
10. 10
    SecadoThe ethyl acetate is dried over MgSO4
11. 11
    Otroremoved
12. 12
    Otroto yield a solid residue which
13. 13
    Temperaturato cool for about 16 hours
14. 14
    FiltraciónThe solid is filtered

Procedimiento

A mixture of 14.8 g of glyoxylic acid (in 18.5 cc of water) and 22 g of 2-acetylfuran is heated at 125°-135° C. for about 5 hours; the water is removed as it forms via a Dean Stark tube. The mass cyrstallizes over about a 16 hour period and is dissolved in 600 cc of ethyl acetate and extracted into 600 cc of 10% sodium carbonate. The aqueous solution is treated with activated charcoal and a filter aid, and then filtered. It is made strongly acid with 20% HCl and the solid which precipitates is extracted with ethyl acetate. The ethyl acetate is dried over MgSO4 and removed to yield a solid residue which is dissolved in 100 cc hot acetonitrile and allowed to cool for about 16 hours. The solid is filtered to yield 7.2 g of the title compound, melting point 153°-155° C.

Fuente