Dimethylformamide → 5-[1-(4-Chloro-3-methyl-phenyl)-propylamino]-2-methyl-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of INT 8 (2.20 g, 14.7 mmol) in Et2O (147 mL) at −78° C. was added tBuLi (1.7 M in pentane, 34.7 mL, 59.0 mmol) dropwise. The mixture was stirred at −78° C. for 40 min, then DMF (2.5 mL) was added. The reaction mixture was stirred at −78° C. for an additional 20 minutes. The mixture was quenched with saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/EtOAc) to afford INT 9.

Provenance & Evidence