反応 #1859304

反応方程式

methanol

116c

Methyl 3-(Bromomethyl)thiophene-2-carboxylate

ammonia

→

116d

収率 57.0%

Methyl 3-(Aminomethyl)thiophene-2-carboxylate

収率 57.0%

反応条件

後処理

1. 1
   その他A 2-L single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
2. 2
   その他was purged with nitrogen
3. 3
   濃縮After that time, the reaction mixture was concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in water (150 mL)
5. 5
   抽出extracted with methyl tert-butyl ether (2×25 mL)
6. 6
   抽出extracted with methyl tert-butyl ether (3×150 mL)
7. 7
   乾燥The combined organic layers were dried over sodium sulfate
8. 8
   濃縮concentrated under reduced pressure

実験手順

A 2-L single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with 116c (7.50 g, 32.0 mmol) and a 7 M solution of ammonia in methanol (915 mL, 6.40 mol). The solution was stirred at room temperature for 14 h. After that time, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (150 mL) and extracted with methyl tert-butyl ether (2×25 mL). The aqueous layer was basified with sodium hydroxide (5.00 g) and extracted with methyl tert-butyl ether (3×150 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford a 57% yield (3.14 g) of 116d as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.45 (d, 1H, J=5.1 Hz), 7.14 (d, 1H, J=5.1 Hz), 4.11 (s, 2H), 3.88 (s, 3H), 1.72 (br s, 2H); MS (ESI+) m/z 172.0 (M+H). The material was used without further purification.

出典