反応 #42387

反応方程式

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

lithium hydroxide monohydrate

→

title compound

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

溶媒

dioxane methanol water

反応条件

後処理

1. 1
   濃縮The reaction mixture is concentrated under reduced pressure
2. 2
   その他the solid residue partitioned between ethyl acetate and water The aqueous phase
3. 3
   抽出extracted several times with 3:1 chloroform/2-propanol
4. 4
   洗浄The combined organic phase is washed with water, and brine
5. 5
   乾燥dried (sodium sulfate)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure

実験手順

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).

出典