Water → Ethyl 3-(4-(methoxymethoxy)phenyl)propiolate

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Under an Ar atmosphere, a mixture of 1-iodo-4-(methoxymethoxy)benzene (500 mg, 1.89 mmol), Ethyl propiolate (371 mg, 3.78 mmol) and Copper(I) oxide (270 mg, 1.89 mmol) in DMF (10 ml) was heated at 110° C. for 16 h. After cooling, H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with H2O, brine, dried over Na2SO4, then concentrated. Purification by silica gel flash column chromatography (eluent: hexane/AcOEt, 15:1) gave 2e (52%). 2e: colorless oil; 1H-NMR (CDCl3) δ 1.36 (3H, t, J=7.1), 3.48 (3H, 2), 4.29 (2H, q, J=7.1), 5.20 (2H, s), 7.02 (2H, d, J=8.8 Hz), 7.54 (2H, d, J=8.8 Hz).

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