Dimethylformamide → 4-(Octynyl)-3-thiophenecarboxaldehyde

Beteiligte Stoffe

Reaktionsschritte

3-Bromo-4-(1-octynyl)thiophene (2.0 g, 7.38 mM) was dissolved in dry tetrahydrofuran under argon. Butyl lithium (2.85 ml of a 2.6M hexane solution) was added keeping the temperature at -20° C. After 30 min at this temperature, N,N-dimethl formamide (2 ml) was added and the mixture allowed to attain room temperature overnight. Hydrolysis and extraction with ether yielded a yellow oil (1.70 g) which was purified by chromatography on silica eluting with chloroform/hexane (1:1). This gave 550 mg (34%) of the title compound as a yellow oil. νmax (film) 3100, 2225, 1680, 880, 760, 670; δ(CDCl3) 0.93(3H, t, J=6 Hz), 1.3(8H, m), 2.2(2H, t, 6 Hz), 7.25(1H, s), 7.67(1H, s), 9.93(1H, s).

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