Magnesium → HCID 131732020, compound

Participants

Reaction Steps

To a MeOH solution (0.1 M) of 1-(1,1-dimethylethyl) 3-ethyl 2′-(methyloxy)-5,6-dihydro-4,4′-bipyridine-1,3(2H)-dicarboxylate (1 eq.) from the previous step was added magnesium turnings (3.3 eq.). The suspension was evacuated and back-filled with N2. Finally, the reaction mixture was sonicated at RT for 3.5 h during which the magnesium turnings disappeared. The reaction was then quenched with the addition of diethyl ether and sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 90:10 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Provenance & Evidence