Potassium Carbonate → HCID 22563203, compound

Participants

Reaction Steps

A slurry of 1-(2-(4-cyano-phenyl)-2-oxo-ethyl)-pyridinium bromide (11) (4.04 grams, 13.2 mmol) and potassium carbonate (2.21 grams, 16.0 mmol) in tetrahydrofuran (250 mL) was stirred at room temperature for 10 minutes. To it was added 3-butyn-2-one (1.4 mL, 16.0 mmol), and the reaction mixture was kept stirring at room temperature for 6 hours. The insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was subjected to column chromatographic purification on silica gel using 3:1 hexane and ethyl acetate (Rf 0.2) to afford 1-acetyl-3-(4-cyanobenzoyl)indolizine (12) as a yellow solid (2.55 grams, 72%). 1H NMR (CDCl3) δ 2.56 (s, 3H), 7.23 (m, 1H), 7.62 (m, 2H), 7.90 (m, 4H), 8.72 (d, J=9.0, 1H), 10.02 (d, J=6.6, 1H); ESMS calcd (C18H12N2O2): 288.1. found: 289.1 (M+H)+.

Provenance & Evidence