Diisobutylaluminum hydride → HCID 90456193, compound

Participants

Reaction Steps

To a solution of ethyl 5-(4-cyanophenyl)oxazole-4-carboxylate (500 mg, 2.06 mmol, 1.00 equiv) in anhydrous THF (10 mL) maintained under nitrogen at −78° C. was added dropwise a 25% solution of DIBAL (2.5 mL) in toluene with stirring. The resulting solution was stirred at −40° C. for 3 h and then quenched by the addition of 10 mL of water. The mixture was extracted with 2×10 mL of ethyl acetate. The combined organic layers was washed with 1×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to yield 350 mg (86%) of 4-(4-formyloxazol-5-yl)benzonitrile as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 10.16 (s, 1H), 8.42 (d, J=8.4 Hz, 2H), 8.04 (s, 1H), 7.83 (d, J=8.4 Hz, 2H) ppm.

Provenance & Evidence