Tetrahydrofuran → HCID 58195999, compound

Participants

Reaction Conditions

Reaction Steps

A solution of chloroenone 16 (140 mg, 1.2 mmol, 1.1 equiv) in tetrahydrofuran (3.5 mL) at 25° C. was transferred via cannula to a stirred solution of aziridine 13 (130 mg, 1.1 mmol, 1.0 equiv) and triethylamine (0.19 mL, 1.4 mmol, 1.2 equiv) in tetrahydrofuran (4.0 mL) at 25° C. The reaction vessel was sealed under argon and heated to 60° C. via oil bath for 24 h. The reaction mixture was cooled to 25° C. and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (5% triethylamine in ethyl acetate) to afford 17 (130 mg, 58% yield) as a brown oil. Rf=0.56 (5% triethylamine in ethyl acetate); 1H NMR (500 MHz, C6D6) δ 7.05-7.15 (m, 5H, ArH), 5.39 (t, 1H, J=1.5 Hz, vinyl H), 2.41 (dd, 1H, J=6, 3 Hz, ArCHN), 2.08 (m, 2H, CH2), 1.85-1.95 (m, 2H, CH2), 1.73 (dd, 1H, J=3, 1 Hz, CH2N), 1.60 (dd, 1H, J=6, 1 Hz, CH2N).

Provenance & Evidence