Hydroxyamine hydrochloride → 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime

Participants

Reaction Steps

A 1 L three-necked round bottom flask equipped with a magnetic stirrer was dried and cooled under a stream of nitrogen then charged with 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde (15 g, 0.057 mol, 1.0 equiv.), NaOAc (15.67 g, 0.12 mol, 2.0 equiv.), hydroxyamine hydrochloride (8.01 g, 0.12 mol, 2.0 equiv.) and MeOH (300 mL) and the reaction mixture was stirred at RT for 1 h. The reaction mixture was then concentrated and the residue was dissolved in EtOAc (1000 mL). The organic layer was washed with water (2×300 mL) and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime (14.5 g, 93% yield).

Provenance & Evidence