Acetic Acid → HCID 53915788, compound

Participants

Reaction Steps

Acetic acid (16 mL) was added to a suspension of 1-(3-pyridyl)-3-(4-oxanyl)propan-1-one oxime (1.60 g, 6.83 mmol) in 95% ethanol (40 mL) over a period of 15 min. Zinc dust (12 g, 180 mmol) was added and the reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was filtered through a Celite plug, which was then washed with ethanol (50 mL). The combined filtrates were concentrated by rotary evaporation. The solid residue was made basic by addition of 50% aqueous NaOH (with ice bath cooling), saturated with solid NaCl and extracted with chloroform (5×30 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to give pure product as a colorless viscous liquid (1.40 g, 82% yield).

Provenance & Evidence