Ethyl propiolate → HCID 68494694, compound

Participants

Reaction Steps

To a solution of 2-azido-N-benzyl-4-methylthiazole-5-carboxamide (1.00 g, 3.67 mmol) in tetrahydrofuran (30 mL) was added copper(I) iodide (0.70 g, 3.67 mmol), N,N-diisopropylethylamine (1.28 mL, 7.32 mmol) and ethyl propiolate (0.45 g, 4.58 mmol). The reaction mixture was stirred at ambient temperature for 18 hours and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:petroleum ether, 1:1) to afford the title compound as a white solid in 61% yield (0.83 g): 1H NMR (300 MHz, CDCl3) δ 8.87 (s, 1H), 7.36-7.26 (m, 5H), 6.17 (br s, 1H), 4.63 (d, J=6.0 Hz, 2H), 4.47 (q, J=6.0 Hz, 2H), 2.70 (s, 3H), 1.42 (t, J=6.0 Hz, 3H); MS (ES+) m/z 372.3 (M+1).

Provenance & Evidence