Diisobutylaluminum hydride → Quinoxaline-6-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of N-methoxy-N-methylquinoxaline-6-carboxamide (4.34 g, 20 mmol, 1.0 eq.) in THF (40 mL) cooled at −78° C. was added DiBAl—H (40 mL, 40 mmol, 2.0 eq.) dropwise. The resulted mixture was stirred at −78° C. for 30 min, then quenched by the addition of aqueous NH4Cl solution. The mixture was adjusted to pH 7 with HCl (1N, 60 mL) and extracted with EA (50 mL×3). The organic layers were combined, dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified via flash column chromatography (PE/EA=4/1, v/v) to afford quinoxaline-6-carbaldehyde as yellow solid (2.96 g, 93.7%).

Provenance & Evidence