Methyl propiolate → HCID 64534769, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl propiolate (2, 1.314 ml, 15.41 mmol) and copper(I) oxide (1.086 g, 7.59 mmol) in DMF (20 ml) was added 1-iodo-2-methoxybenzene (1, 1.262 ml, 9.48 mmol). The resulting mixture was heated in a Microwave reactor to 110° C. for 2 hrs. The reaction mixture was filtered through a short pad of silica gel and washed w/EtOAc. The organic layer was washed w/1M HCl, brine and sat'd NaHCO3, dried (Na2SO4) and concentrated to leave an oil as crude product, which was purified by flash chromatography (SiO2, EtOAc/Hexane, 1:2) to afford methyl 3-(2-methoxyphenyl)propiolate 3 (932 mg, 4.66 mmol, 49.1% yield). 1H-NMR (500 MHz, CDCl3), δ: 7.54 (1H, dd), 7.44 (1H, td), 6.98-6.92 (m, 2H), 3.92 (s, 3H), 3.86 (s, 3H).

Provenance & Evidence