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

Temperature

80 °C

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).

1. temperatureThe mixture was cooled to room temperature
2. washwashed with water
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. dissolutionThe resulting residue was dissolved in ethanol (3 mL)
6. stirringTHF (3 mL), and the mixture was stirred at room temperature for 2 hours
7. extractionextracted with ethyl acetate
8. washThe organic layer was washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe residue obtained upon concentration under reduced pressure
11. customwas then purified by silica gel column chromatography

ORD record

ord-09979fbf166e43feacbbecbf08dff1f0

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998954B2