反应 #42387

反应方程式

methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate

lithium hydroxide monohydrate

→

title compound

5-{[Butyl(methyl)amino]methyl}thiophene-2-carboxylic acid

溶剂

dioxane methanol water

反应条件

后处理

1. 1
   浓缩The reaction mixture is concentrated under reduced pressure
2. 2
   其他the solid residue partitioned between ethyl acetate and water The aqueous phase
3. 3
   萃取extracted several times with 3:1 chloroform/2-propanol
4. 4
   洗涤The combined organic phase is washed with water, and brine
5. 5
   干燥dried (sodium sulfate)
6. 6
   过滤filtered
7. 7
   浓缩concentrated under reduced pressure

实验过程

To a solution of methyl 5-{[butyl(methyl)amino]methyl}thiophene-2-carboxylate (280 mg, 1.16 mmol) in 2:1:1 dioxane/methanol/water (8.0 mL) is added lithium hydroxide monohydrate (146 mg, 3.38 mmol) and the reaction mixture stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure and the solid residue partitioned between ethyl acetate and water The aqueous phase is acidified to pH 1 with 1 N hydrochloric acid and extracted several times with 3:1 chloroform/2-propanol. The combined organic phase is washed with water, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the title compound in pure form. 1H NMR (300 MHz, CD3OD) δ 7.75 (d, J=4 Hz, 1H), 7.41 (d, J=4 Hz, 1H), 4.63 (s, 2H), 3.20-3.14 (m, 2H), 2.85 (s, 3H), 1.82-1.72 (m, 2H), 1.42 (tq, J 8, 7 Hz, 2H), 0.99 (t, J=7 Hz, 3H).

来源