Tetrahydrofuran → HCID 86652147, compound

Participants

Reaction Conditions

Reaction Steps

A solution of chloroenone 16 (16 mg, 0.14 mmol, 1.0 equiv) in tetrahydrofuran (1.0 mL) at 25° C. was transferred via cannula to a stirred solution of aziridine 14 (25 mg, 0.17 mmol, 1.2 equiv) and triethylamine (35 μL, 0.25 mmol, 1.5 equiv) in tetrahydrofuran (1.0 mL) at 25° C. The resulting brown solution was stirred at 25° C. for 24 h. The reaction mixture was concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (5% triethylamine and 20% ethyl acetate in benzene) to afford 18 (5 mg, 16% yield) as a yellow film. Rf=0.29 (5% triethylamine and 20% ethyl acetate in benzene); 1H NMR (500 MHz, C6D6) δ 7.00 (m, 2H, ArH), 6.76 (m, 2H, ArH), 5.43 (t, 1H, J=1.5 Hz, vinyl H), 3.28 (s, 3H, OCH3), 2.45 (dd, 1H, J=6, 3 Hz, ArCHN), 2.11 (m, 2H, CH2), 1.85-2.00 (m, 2H, CH2), 1.77 (dd, 1H, J=3, 1 Hz, CH2N), 1.63 (dd, 1H, J=6, 1 Hz, CH2N).

Provenance & Evidence