Diethyl Malonate → HCID 18404089, compound

Participants

Reaction Steps

A solution of 3-[(triphenylphosphoranylidene)amino]-2-thiophenecarbaldehyde (11-2, 2.50 g, 6.45 mmol, 1 equiv), diethyl malonate (1.96 mL, 12.9 mmol, 2.00 equiv), and piperidine (0.319 mL, 3.23 mmol, 0.500 equiv) in EtOH (50 mL) was heated at reflux for 16 h. The reaction mixture was concentrated, and the residue was purified by flash column chromatography (heaxane, initally, grading to 30% EtOAc in hexane) to give ethyl 5-ethoxythieno[3,2-b]pyridine-6-carboxylate (11-3) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 7.84 (d, 1H, J=7.4 Hz), 7.37 (d, 1H, J=7.2 Hz), 4.55 (q, 2H, J=7.0 Hz), 4.40 (q, 2H, J=7.1 Hz), 1.48 (t, 3H, J=7.0 Hz), 1.41 (t, 3H, J=7.1 Hz).

Provenance & Evidence