Sodium borohydride → HCID 54140687, compound

Participants

Reaction Steps

Sodium borohydride (0.13 g, 0.0034 mol) was added to a mixture of methanol (5 ml) and water (5 ml) at 0° C. To this was added dropwise a solution of α-(methoxyimino)-α-(1-oxopyridinium-3-yl)acetonitrile (D5) (0.2 g, 0.0011 mol) in methanol (30 ml) and water (5 ml). The mixture was allowed to warm to room temperature and stirred for a further 2 h. The mixture was evaporated to dryness and the residue partitioned between saturated aqueous potassium carbonate (25 ml) and chloroform(3×30 ml). The organic extracts were combined and dried (Na2SO4) then filtered and evaporated to dryness. The residue was subjected to column chromatography on silica gel eluting with 0-2% methanol/chloroform to give a solid which was recrystallised from ethyl acetate/pentane to afford the title compound (E2) as a white crystalline solid (0.135 g, 67%) m.p. 145°-147° C.

Provenance & Evidence