Hexane → HCID 14743045, compound

Participants

Reaction Steps

To a stirred solution of 2-bromothiophene (10 g, 61.34 mmol) in dry THF (42 ml) was dropwise added a solution of n-butyl lithium in n-hexane (1.6M, 42.0 ml, 67.48 mmol) at −78° C. The resulting suspension was stirred at the same temperature for 30 min. After 30 min, a solution of isonicotinaldehyde (6.56 g, 61.34 mmol) in dry THF (30 ml) was dropwise added and continued the stirring at −78° C. for another 2 h. The progress of the reaction was monitored by TLC. The reaction was quenched with NH4Cl solution (10 ml) and diluted with diethyl ether (500 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over anhydrous Na2SO4 and evaporated. The crude compound was triturated with hexane and diethyl ether to get the desired compound as an off-white solid (4.0 g, 34%). 1H NMR (400 MHz, DMSO-d6) δ 8.52 (dd, J=4.9, 1.5 Hz, 2H), 7.45-7.38 (m, 3H), 6.97-6.93 (m, 2H), 6.45 (d, J=4.4 Hz, 1H), 5.97 (d, J=4.4 Hz, 1H).

Provenance & Evidence