Hydrochloric Acid → HCID 87694888, compound

Participants

Reaction Conditions

Reaction Steps

2-Methoxy-5-acetylpyridine (12.1 g) and t-butyl nitrite (9.92 g) were dissolved in THF (120 ml). The solution was cooled at 0-5° C. To the solution was added t-BuOK (10.8 g) at 5-25° C. The reaction mixture was stirred at 25° C. for 2 hours. To the mixture was added 1N HCl (105 ml). The solution was portioned to EtOAc and water. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic solution was washed with 10% aq. NaOAc and brine successively, dried over MgSO4. Evaporation of solvent in vacuo gave solid residue. The residue was pulverized with IPE (150 ml). The precipitated crystals were collected by filtration, to give (1E)-(6-methoxy-3-pyridyl)(oxo)acetaldehyde oxime as a solid (5.45 g) (anti, syn mixture (anti:syn=1:1)). Evaporation of solvent in the filtrate gave a residue. The residue was pulverized with IPE. The precipitated crystals were collected by filtration, to give (1E)-(6-methoxy-3-pyridyl)(oxo)acetaldehyde oxime as a solid (2.5 g) (anti, syn mixture (anti:syn=1:1)).

Provenance & Evidence