Reacción #1925

Ecuación de reacción

3-acetamidophenol

cesium carbonate

sodium bicarbonate

methyl 3-bromomethyl-2-thiophenecarboxylate

→

methyl 3-(3-acetamidophenoxymethyl)-2-thiophenecarboxylate

Rendimiento 75.1%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred overnight at room temperature
2. 2
   Extracciónfollowed by extraction with ethyl acetate
3. 3
   LavadoThe organic layer was washed with a saturated aqueous solution of sodium chloride
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   FiltraciónAfter the drying agent was filtered off
6. 6
   Concentraciónthe organic layer was concentrated under reduced pressure
7. 7
   OtroThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Procedimiento

To a solution of 3-acetamidophenol (4.79 g, 31.7 mmol) in dimethylformamide (50 ml) was added cesium carbonate (5.67 g, 17.4 mmol), followed by stirring at room temperature for 30 minutes. To the resulting mixture was added methyl 3-bromomethyl-2-thiophenecarboxylate (8.94 g, 38.0 mmol), and the mixture was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was poured into a 5% aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), followed by trituration with hexane to give methyl 3-(3-acetamidophenoxymethyl)-2-thiophenecarboxylate as a white solid (7.27 g, 75%).

Fuente