تفاعل #42387

معادلة التفاعل

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

lithium hydroxide monohydrate

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title compound

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

المذيبات

dioxane methanol water

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture is concentrated under reduced pressure
2. 2
   أخرىthe solid residue partitioned between ethyl acetate and water The aqueous phase
3. 3
   استخلاصextracted several times with 3:1 chloroform/2-propanol
4. 4
   غسيلThe combined organic phase is washed with water, and brine
5. 5
   تجفيفdried (sodium sulfate)
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

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).

المصدر