Terephthalaldehyde → 4-[(5-Ethyl-4-phenyl-thiophen-2-yl)-3-oxo-propenyl]-benzaldehyde

Participants

Reaction Steps

A solution of 1-(5-ethyl-4-phenyl-thiophen-2-yl)-ethanone (600 mg, 2.61 mmol) and terephthalaldehyde (874 mg, 6.51 mmol) in ethanol (10 mL) and 5 N HCl in isopropanol (5 mL) is stirred at rt for 3 days. The reaction mixture is diluted with water and extracted with diethyl ether. The organic extract is washed with water and sat. aq. NaHCO3 solution and the solvent is evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 4-[3-(5-ethyl-4-phenyl-thiophen-2-yl)-3-oxo-propenyl]-benzaldehyde (280 mg) as a yellow solid, LC-MS: tR=1.14 min, [M+1]+=347.14, 1H NMR (CDCl3): δ 10.05 (s, 1H), 7.95-7.88 (m, 2H), 7.84-7.77 (m, 3H), 7.52-7.35 (m, 5H), 2.96 (q, J=7.6 Hz, 2H), 1.35 (t, J=7.6 Hz, 3H).

Provenance & Evidence