反応 #1509607

反応方程式

3-Chloro-1,2-propanediol

Imidazole

potassium hydroxide

potassium iodide

→

solid

収率 96.0%

1-(2,3-Dihydroxypropyl)-imidazole

収率 96.0%

溶媒

CH3CN

CH3CN

反応条件

後処理

1. 1
   温度at reflux for 24 h
2. 2
   ろ過was then filtered through Celite
3. 3
   濃縮concentrated
4. 4
   温度heated
5. 5
   温度to reflux
6. 6
   workup.STIRRINGstirred overnight
7. 7
   その他decanted
8. 8
   洗浄wash process

実験手順

Imidazole (3.40 g, 50.0 mmol), pulverized potassium hydroxide (5.61 g, 100 mmol), and potassium iodide (8.30 g, 50.0 mmol) were suspended in CH3CN (100 mL). 3-Chloro-1,2-propanediol (8.29 g, 75.0 mmol) was added, and the mixture was stirred at reflux for 24 h. After cooling to room temperature, additional CH3CN (150 mL) was added to the reaction, which was then filtered through Celite and concentrated. The crude product was then suspended in CH2Cl2 (250 mL), heated to reflux and stirred overnight, and then decanted. The product was still slightly impure by 1H NMR, so the CH2Cl2 wash process was repeated once, to afford a white solid (6.82 g, 96%) after drying in vacuo. 1H NMR (400 MHz, DMSO) δ 7.54 (t, J=1.0 Hz, 1H), 7.11 (t, J=1.2 Hz, 1H), 6.84 (t, J=1.0 Hz, 1H), 5.08 (s, 1H), 4.83 (s, 1H), 4.05 (dd, J=13.9, 3.6 Hz, 1H), 3.84 (dd, J=14.0, 7.2 Hz, 1H), 3.70-3.58 (m, 1H), 3.31 (dt, J=13.8, 9.0 Hz, 3H), 3.19 (dd, J=11.0, 6.5 Hz, 1H).

出典