Oxazole → 2-Phenyl-1,3-oxazole

Participants

Reaction Steps

To a solution of oxazole (0.5 g, 7 mmol) in anhydrous THF (10 mL) was added n-BuLi (3.5 mL, 8.8 mmol) dropwise at −65° C. After stirring for 10 min, anhydrous ZnCl2 (2 g, 14.7 mmol) was added. The reaction mixture was allowed to warm to room temperature. Then Pd(PPh3)4 (0.3 g, 0.26 mmol) and iodobenzene (2 g, 9.8 mmol) were added. The reaction mixture was heated at 60° C. for 1 h. After quenching with water (20 mL), the solution was extracted with EtOAc (20 mL×3). The combined organic layers were dried over Na2SO4 and filtered. The filtrate was concentrated and purified by column chromatography to give 600 mg of the desired product. LC-MS: m/z 146 (M+H+).

Provenance & Evidence