Dimethylformamide → 5-(Phenylsulfanyl)thiophene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-phenylthiothiophene (3.87 g) in dry tetrahydrofuran (50 ml) at -30° C. under N2, was added dropwise, n-butyllithium (8.0 ml, 2.5M) and the solution left to stir at -30° C. for 2 hours. Dry dimethylformamide (2.32 ml) was then added and the solution allowed to stir at -30° C. for a further hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with 2N HCl (50 ml), extracted with ether (2×50 ml), dried over MgSO4 and evaporated under reduced pressure to give an orange oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using 20% ether-hexane to give a pale yellow oil.

Provenance & Evidence