N-Formylmorpholine → 4-(4-Benzyl-morpholin-2-yl)-benzaldehyde

Participants

Reaction Steps

To a solution of 4-benzyl-6-(4-bromo-phenyl)-morpholine (1.73 g; 5.21 mmol) in THF (25 mL) was added dropwise n-BuLi (2.08 mL; 2.50 mol/l; 5.21 mmol), at −78° C. The resulting mixture was stirred for one hour, and subsequently a solution of N-formylmorpholine (0.90 g; 7.81 mmol) in THF (5 mL) was added dropwise, at −78° C. The reaction was quenched by the addition of an 5% aqueous NaHCO3 solution, at −70° C. The resulting mixture was extracted with Et2O. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O: hexanes 1:1) to afford 4-(4-benzyl-morpholin-2-yl)-benzaldehyde (1.21 g).

Provenance & Evidence