Diisobutylaluminum hydride → HCID 86677485, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-methyl-1-phenyl-1H-pyrazole-3-carboxylate (100 mg, 434 μmol) in toluene (1 mL) cooled to −78° C. was added dropwise DIBAL-H (1M solution in toluene, 868 μL, 868 μmol) keeping the temperature below −68° C. The reaction mixture was stirred at −78° C. for 30 min and at −15° C. for 1 h. At that temperature, KHSO4 (10% aqueous solution, 10 mL) was added dropwise and the resulting reaction mixture was extracted with ethyl acetate (2×50 mL). The organic phases were washed with water (1×30 mL) and brine (1×20 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 112 mg crude material. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as yellow viscous oil (52 mg, 276 μmol, 63.6%).

Provenance & Evidence