Ethanol → 4-(5-Ethoxy-2-fluoro-phenyl)-5,6-dimethyl-pyridine-2-carbaldehyde

Participants

Reaction Steps

1M DIBAL in toluene (8.7 mL, 8.7 mmol) was added dropwise over 12 minutes to a stirred solution of methyl 4-(5-ethoxy-2-fluoro-phenyl)-5,6-dimethyl-pyridine-2-carboxylate (which may be prepared as described in Description 52) (1.32 g, 4.35 mmol) in dry THF (25 mL) at −75° C. The reaction was stirred at this temp for 2.5 h then EtOH (0.2 ml) was added to quench. After 1 minute the reaction was poured into saturated Rochelle salt solution (200 ml). The mixture was extracted with EtOAc (100 ml) then DCM (2×100 ml). The combined organic extracts were dried (Na2SO4), filtered and evaporated to a white solid, which was dried at RT under vacuum for 16 h to afford 4-(5-ethoxy-2-fluoro-phenyl)-5,6-dimethyl-pyridine-2-carbaldehyde (D53) (1.17 g);

Provenance & Evidence