Reaction #1509607

Reaction equation

3-Chloro-1,2-propanediol

Imidazole

potassium hydroxide

potassium iodide

→

solid

Yield 96.0%

1-(2,3-Dihydroxypropyl)-imidazole

Yield 96.0%

Solvents

CH3CN

CH3CN

Conditions

Workup

1. 1
   Temperatureat reflux for 24 h
2. 2
   Filtrationwas then filtered through Celite
3. 3
   Concentrationconcentrated
4. 4
   Temperatureheated
5. 5
   Temperatureto reflux
6. 6
   workup.STIRRINGstirred overnight
7. 7
   Otherdecanted
8. 8
   Washwash process

Procedure

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).

Source