反応 #1922

反応方程式

sodium bicarbonate

methyl 2-bromomethylbenzoate

3-acetamidophenol

cesium carbonate

→

methyl 2-(3-acetamidophenoxymethyl)benzoate

収率 61.2%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred overnight at room temperature
2. 2
   抽出followed by extraction with ethyl acetate
3. 3
   洗浄The organic layer was washed with a saturated aqueous solution of sodium chloride
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   ろ過After the drying agent was filtered off
6. 6
   濃縮the organic layer was concentrated under reduced pressure
7. 7
   その他The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

実験手順

To a solution of 3-acetamidophenol (1.0 g, 6.6 mmol) in dimethylformamide (10 ml) was added cesium carbonate (1.3 g, 3.9 mmol), followed by stirring at room temperature for 30 minutes. To the resulting mixture was added methyl 2-bromomethylbenzoate (1.8 g, 7.9 mmol), and the mixture was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was poured into a5% 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=4/1), followed by trituration with hexane to give methyl 2-(3-acetamidophenoxymethyl)benzoate as a white solid (1.21 g, 61%).

出典