Triethylamine → 5-Cyano-2-(3-iodophenyl)-1,3-oxazole

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Reaction Steps

5-Formyl-2-(3-iodophenyl)-1,3-oxazole (200 mg, 0.668 mmol) obtained in Step 1 was dissolved in dichloromethane (8 mL), and the mixture was stirred at room temperature for 3.5 hours after adding hydroxylamine hydrochloride (56.0 mg, 0.803 mmol) and triethylamine (0.112 mL, 0.803 mmol). A saturated aqueous sodium bicarbonate solution was added to the mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (10 mL), cooled to 0° C., and stirred at 0° C. for 1 hour after adding 2-chloro-1,3-dimethylimidazolium chloride (136 mg, 0.802 mmol) and triethylamine (0.224 mL, 1.61 mmol). Thereafter, water was added to the mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 5-cyano-2-(3-iodophenyl)-1,3-oxazole (137 mg, 70%).

Provenance & Evidence