Sodium borohydride → HCID 59648505, compound

Participants

Reaction Steps

Under a N2 and at rt, to a 40-mL scintillation vial fitted with a magnetic stir bar was added ethyl 2-(4-chlorobenzoyl)-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.203 g, 0.61 mmol) in solution in 5 mL in THF. AlCl3 (0.22 g, 1.67 mmol, 2.75 equiv) and NaBH4 (0.116 g, 3.0 mmol, 5 eq.) are added in the same time. The mixture was heated to reflux for 2 h. The reaction was cooled to rt and solvent was evaporated. The crude product was purified via ISCO Companion (0-30% EtOAc/heptane over 30 min) to give ethyl 2-(4-chlorobenzyl)-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.050 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.39 (t, J=7.13 Hz, 3H) 4.11 (s, 2H) 4.37 (q, J=7.13 Hz, 2H) 6.71 (s, 1H) 7.00 (d, J=1.76 Hz, 1H) 7.18-7.23 (m, 2H) 7.27-7.32 (m, 2H) 9.41 (s, 1H).

Provenance & Evidence