Réaction #4495

Équation de réaction

benzamide

ethyl 4-chloroacetoacetate

sodium bicarbonate

→

ethyl 2-phenyl-4-oxazoleacetate

Rendement 38.0%

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Extractionthe mixture was extracted with ethyl acetate
3. 3
   LavageThe extract was washed with water
4. 4
   Séchagedried (MgSO4)
5. 5
   Concentrationconcentrated
6. 6
   AutreThe residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9)

Mode opératoire

A mixture of benzamide (60.0 g) and ethyl 4-chloroacetoacetate (49.4 g) was heated at 120° C. for 2 hours. After cooling, aqueous sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9) to yield ethyl 2-phenyl-4-oxazoleacetate as an oil (26.4 g, 28.0%). NMR (CDCl3)δ: 1.27 (3H, t, J=7 Hz), 3.68 (3H, s), 4.15 (2H, q, J=7 Hz), 7.4 (3H, m), 7.67 (1H, s), 8.0 (2H, m).

Source