Dimethylformamide → HCID 18923847, compound

Participants

Reaction Steps

To a solution of 3-bromo-2,5-diethyl thiophene, C6, (9.1 g, 41 mmol) in 100 mL of dry Et2O cooled to -78° C. was added n-BuLi (26.2 mL, 42 mmol) dropwise. The bath temperature was allowed to rise to -20° C. and DMF (6.3 mL, 82 mmol) was added. The reaction mixture was allowed to warm to room temperature overnight. The reaction was quenched with NH4Cl (aq) and extracted with Et2O. The organic layer washed twice with water and brine and then dried (MgSO4). After evaporation of solvent, the crude product was purified on flash silica gel (98:2 hexane/Et2O) to afford 2,5-diethylthiophene-3-carboxaldehyde, D6, as a light yellow oil (5.0 g, 72%). 1H NMR (CDCl3) supported the assigned structure. ##STR51##

Provenance & Evidence