반응 #1509607

반응 방정식

3-Chloro-1,2-propanediol

Imidazole

potassium hydroxide

potassium iodide

→

solid

수율 96.0%

1-(2,3-Dihydroxypropyl)-imidazole

수율 96.0%

용매

CH3CN

CH3CN

반응 조건

후처리

1. 1
   온도at reflux for 24 h
2. 2
   여과was then filtered through Celite
3. 3
   농축concentrated
4. 4
   온도heated
5. 5
   온도to reflux
6. 6
   workup.STIRRINGstirred overnight
7. 7
   기타decanted
8. 8
   세척wash process

실험 절차

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).

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