Sulfuric Acid → 4-(2-Cyclopropyl-1,3-oxazol-4-yl)benzaldehyde

Participants

Reaction Steps

To a 0C solution of 4-(2-cyclopropyl-1,3-oxazol-4-yl)benzonitrile (0.984 g, 4.68 mmol) in anhydrous CH2Cl2 (3 ml) was added dropwise a 1M solution of DIBAL in CH2Cl2 (5.60 ml, 1.22 mmol). Upon completion of addition, the solution was warmed to 45C for 3 h. The solution was cooled and 10% aqueous H2SO4 was slowly added until pH<4. The mixture was stirred overnight at rt. The aqueous phase was extracted with CH2Cl2 (3×40 ml). The combined organic phases were dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (EtOAc/hexanes, 1:4) to yield the title compound as a yellow solid (0.92 g, 92%).

Provenance & Evidence