Triethylamine → ethyl 2-(5-methyl-2,3-diphenyl-1H-pyrrol-1-yl)acetate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-aminoacetate hydrochloride (0.548 g, 3.92 mmol) was diluted with Ethanol (10 ml) then charged with triethylamine (0.746 ml, 5.35 mmol) and 1,2-diphenylpentane-1,4-dione (0.900 g, 3.57 mmol), added as a solution in DCM. The reaction was heated at 100° C. overnight, after which TLC showed a new spot (less polar, Rf˜0.9 in 20% EtOAc/hexanes). The reaction was diluted with 10 mL DCM and washed with water (10 mL). The aqueous layer was back-extracted with DCM (10 mL×2). The organics were combined, dried, filtered, and concentrated to yield a crude orange oil. This oil was loaded on a SiO2 column and purified using a 0-20% gradient of EtOAc in hexanes, affording ethyl 2-(5-methyl-2,3-diphenyl-1H-pyrrol-1-yl)acetate (0.780 g, 2.442 mmol, 68.5% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.37-7.33 (m, 3H), 7.27-7.24 (m, 2H), 7.16-7.11 (m, 4H), 7.07-7.04 (m, 1H), 6.24 (b, 1H), 4.42 (s, 2H), 4.21 (q, 2H), 2.27 (s, 3H), 1.25 (t, 3H).

Provenance & Evidence