Reaktion #60027

Reaktionsgleichung

acid

4-(2-furyl)benzoic acid

potassium ethyl malonate

magnesium chloride

THF

→

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

Lösungsmittel

oxalyl chloride

acetonitrile

acetonitrile

triethylamine

Triethylamine

oxalyl chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturReflux
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   Sonstigeto give the crude acid chloride
4. 4
   Einengenconcentrated to dryness
5. 5
   SonstigeThe residue was partitioned between toluene and 10% aqueous HCl
6. 6
   WaschenThe organic layer was washed with 10% HCl and water
7. 7
   Sonstigedried
8. 8
   Einengenwas then concentrated

Vorschrift

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.

Quelle