Dimethyl acetylenedicarboxylate → HCID 76721669, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl acetylene dicarboxylate (75 μL, 0.61 mmol, 1.0 equiv) was added via syringe to a stirred solution of aziridine 15 (100 mg, 0.61 mmol, 1.0 equiv) in tetrahydrofuran (1.0 mL) at 25° C. The resulting bright yellow solution was stirred at 25° C. for 2 d. The reaction mixture was concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (1% triethylamine and 24% ethyl acetate in benzene) to afford 26 (110 mg, 57% yield, 3:1 E:Z mixture) as a yellow film. E-26: Rf=0.31 (1% triethylamine and 24% ethyl acetate in benzene); 1H NMR (500 MHz, C6D6) δ 6.64 (m, 1H, ArH), 6.52-6.54 (m, 2H, ArH), 5.30 (s, 1H, vinyl H), 5.22-5.25 (m, 2H, OCH2O), 3.52 (s, 3H, OCH3), 3.34 (s, 3H, OCH3), 2.84 (dd, 1H, J=6, 3.5 Hz, ArCHN), 1.84 (d, 1H, J=6 Hz, CH2N), 1.71 (d, 1H, J=3.5 Hz, CH2N).

Provenance & Evidence