2-Thiophenecarboxaldehyde → Thiophene, 2-(2-phenylethenyl)-

Participants

Reaction Conditions

Reaction Steps

Benzyldiethylphosphonate (5.7 g, 25 mmol) was dissolved in THF (50 mL) and cooled to -78° C. and nBuLi (2.5 M in hexane, 25 mmol) was added dropwise and the mixture was stirred for 30 min. Then a solution of thiophene-2-carboxaldehyde (2.8 g, 25 mmol) in THF (10 mL) was added dropwise at -78° C. The cold bath was removed and the reaction was warmed to room temperature, heated for 2 h at reflux and the reaction was then cooled and saturated aqueous NH4Cl was added. The mixture was diluted with water and extracted with ether. The organic extract was washed with brine, dried over MgSO4, filtered, and concentrated to provide a solid which was purified by recrystallization from hexane to give 2.6 g of intermediate.

Provenance & Evidence