Реакция #1925

Уравнение реакции

3-acetamidophenol

cesium carbonate

sodium bicarbonate

methyl 3-bromomethyl-2-thiophenecarboxylate

→

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

Выход 75.1%

Растворители

dimethylformamide

Условия реакции

Обработка

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

Методика

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%).

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