Reacción #1509607

Ecuación de reacción

3-Chloro-1,2-propanediol

Imidazole

potassium hydroxide

potassium iodide

→

solid

Rendimiento 96.0%

1-(2,3-Dihydroxypropyl)-imidazole

Rendimiento 96.0%

Disolventes

CH3CN

CH3CN

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 24 h
2. 2
   Filtraciónwas then filtered through Celite
3. 3
   Concentraciónconcentrated
4. 4
   Temperaturaheated
5. 5
   Temperaturato reflux
6. 6
   workup.STIRRINGstirred overnight
7. 7
   Otrodecanted
8. 8
   Lavadowash process

Procedimiento

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).

Fuente