Dimethylformamide → 1-(Triisopropylsilyl)-1H-pyrrole-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-1-(triisopropylsilyl)-1H-pyrrole (2.0 g, 6.61 mmol) in THF (30 mL) was added n-butyllithium (2.5 M in hexanes, 3.4 mL, 8.60 mmol) at −78° C. The mixture was stirred at −78° C. for 10 min then DMF (0.76 mL, 9.92 mmol) was added and the mixture was warmed to 0° C. over 1 hour. The reaction mixture was quenched by saturated NH4Cl and extracted with EtOAc (200 mL). The organic phase was washed with brine then dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-10% EtOAc in hexanes) to afford the sub-title compound (1.65 g, 100%).

Provenance & Evidence