Hydrochloric Acid → 5-Hydroxymethyl-2-(3-iodophenyl)-1,3-oxazole

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Reaction Conditions

Reaction Steps

5-Bromomethyl-2-(3-iodophenyl)-1,3-oxazole (300 mg, 0.824 mmol) obtained in Step 1 was dissolved in acetic acid (8 mL), and the mixture was stirred at 80° C. for 4.5 hours after adding potassium acetate (162 mg, 1.65 mmol). The mixture was cooled to room temperature, diluted with chloroform, and washed with water and a saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in ethanol (3 mL) and THF (3 mL), and the mixture was stirred at room temperature for 2 hours after adding a 1 mol/L aqueous sodium hydroxide solution (4.12 mL, 4.12 mmol). The mixture was neutralized with 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give 5-hydroxymethyl-2-(3-iodophenyl)-1,3-oxazole (247 mg, quantitative).

Provenance & Evidence