Hydrogen Bromide → HCID 68451988, compound

Participants

Reaction Steps

A suspension of 5-(6-methoxy-2-naphthyl)-2-phenyl-1,3-oxazole (433 mg, 1.44 mmol), prepared in the previous step, in 20 mL of glacial acetic acid plus 12 mL of 48% aqueous HBr was stirred under nitrogen at 120° C. for 3 h. The volatiles were removed under reduced pressure. The residue was taken up in 10% methanol in methylene chloride and then made basic by the addition of an excess of 5% NaHCO3. The layers were separated and the aqueous layer extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(2-phenyl-1,3-oxazol-5-yl)-2-naphthol (398 mg, 96%) as a light brown solid, mp 235-238° C. Elemental Analysis for C19H13NO2: Calc'd: C, 79.43; H, 4.56; N, 4.87. Found: C, 78.39; H, 4.76; N, 4.71.

Provenance & Evidence