Ethyl Acrylate → HCID 22503716, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzoyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (5.00 g, 17.2 mmol), cesium carbonate (5.61 g, 17.2 mmol), and ethyl acrylate (1.90 mL, 17.5 mmol) in acetonitrile (250 mL) was heated under N2 at 50° C. for 5 h (reaction can also be run in DMF at room temperature). Cooled to room temperature, diluted with H2O, and extracted with EtOAc. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with EtOAc/hexanes (2: 1) to give 4.82 g (72%) of the title compound as a yellow oil. 1H NMR (CDCl3) δ 7.57-7.38, 7.32, 7.23-7.07, 4.49-4.33, 4.20-4.02, 3.77-3.66, 3.28-3.13, 2.94, 2.72, 1.24; IR (liq.) 2981, 1731, 1631, 1467, 1445, 1422, 1381, 1368, 1349, 1319, 1295, 1272, 1242, 1187, 742, 707 cm−1; MS (ESI) 391.0 (M++H).

Provenance & Evidence