Reacción #60027

Ecuación de reacción

acid

4-(2-furyl)benzoic acid

potassium ethyl malonate

magnesium chloride

THF

→

ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate

Disolventes

oxalyl chloride

acetonitrile

acetonitrile

triethylamine

Triethylamine

oxalyl chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaReflux
2. 2
   Otrothe solvent was removed in vacuo
3. 3
   Otroto give the crude acid chloride
4. 4
   Concentraciónconcentrated to dryness
5. 5
   OtroThe residue was partitioned between toluene and 10% aqueous HCl
6. 6
   LavadoThe organic layer was washed with 10% HCl and water
7. 7
   Otrodried
8. 8
   Concentraciónwas then concentrated

Procedimiento

The acid from Step 1 was converted to the acid chloride by refluxing in a mixture of oxalyl chloride (1.3 ml), THF (20 ml) and several drops of DMF. Small portions of oxalyl chloride were added until the reaction was homogeneous. Reflux continued for 0.5 hours, then the solvent was removed in vacuo to give the crude acid chloride. Meanwhile, potassium ethyl malonate (2.7 g) was reacted with anhydrous magnesium chloride (1.9 g) and triethylamine (2.21 ml) in dry acetonitrile (50 ml) at room temperature for 3 hours. Triethylamine (1 ml) was added, followed by addition of a solution of the acid chloride in acetonitrile. The mixture was then stirred overnight at room temperature, then concentrated to dryness. The residue was partitioned between toluene and 10% aqueous HCl. The organic layer was washed with 10% HCl and water, dried and was then concentrated to give crude ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate as a solid.

Fuente