Ammonium Hydroxide → 4-(Chloromethyl)-2,5-diphenyloxazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methyl-2,5-diphenyloxazole 3-oxide (395 mg, 1.57 mmol) in chloroform (2 mL) was added dropwise a solution of phosphorus oxychloride (265 mg, 161 μL, 1.73 mmol) in chloroform (2.00 mL) over a period of 10 min. The reaction mixture was stirred at 65° C. for 4 h and cooled to 0-5° C. At that temperature, NH4OH (25% aqueous solution, 10 mL) was added dropwise and the mixture was extracted with dichloromethane (3×40 mL). The combined organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and a dichloromethane/heptane gradient) as colorless solid (249 mg, 923 μmol, 58.7%).

Provenance & Evidence