反応 #409410

反応方程式

sodium hydrogen carbonate

3-aminothiophenol

triethylamine

methyl 3-bromomethylthiophene-2-carboxylate

→

methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate

収率 92.3%

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度cooling
2. 2
   洗浄The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate
3. 3
   乾燥a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
4. 4
   ろ過After the drying agent was filtered off
5. 5
   濃縮the organic layer was concentrated under reduced pressure
6. 6
   その他The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

実験手順

To a solution of 3-aminothiophenol (2.3 g, 18.7 mmol) and triethylamine (3.12 ml, 22.4 mmol) in dichloromethane (30 ml) was slowly added methyl 3-bromomethylthiophene-2-carboxylate (6.24 g, 22.4 mmol) under ice-cooling, followed by stirring for 30 minutes. After the reaction was completed, a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and 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=7/1) to give oily methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate (4.82 g, 92%).

出典