Ethanol → HCID 58237096, compound

Participants

Reaction Steps

A mixture of 2-(methoxymethyl)-5-(3-methoxy-4-nitrophenoxy)pyridine (27.0 g), iron (powder, 25.9 g), calcium chloride (1.03 g), ethanol (400 mL) and water (100 mL) was refluxed for 6 h. Then iron (powder, 12.9 g) and calcium chloride (1.03 g) were added to the mixture, and the whole was refluxed for further 2 h. The mixture was cooled to room temperature and filtered with celite. The filtrate was concentrated in vacuo to remove ethanol. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:3 to 3:1, volume ratio) to give the title compound (20.1 g, 83%) as a brown oil. MS 261 (MH+).

Provenance & Evidence