m-Ethynylphenol → Methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (100 mg, 0.34 mmol) and 3-ethynylphenol (0.025 mL, 0.38 mmol) according to the general procedure IC to give 66 mg (69%) of a light brown solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:6→1:0). Rf=0.24 (EtOAc:PE; 1:2); 1H NMR (CDCl3): δ 7.43 (d, J=8.0 Hz, 2H), 7.20-7.15 (m, 3H), 7.10-7.08 (m, 1H), 7.00-6.99 (m, 1H), 6.84-6.80 (m, 1H), 5.50 (br, 1H), 3.68 (s, 3H), 2.96 (t, J=8.0 Hz, 2H), 2.64 (t, J=8.1 Hz, 2H); 13C NMR (CDCl3): δ 173.7, 155.7, 141.0, 132.0, 129.8, 128.5, 124.7, 124.4, 121.3, 118.4, 115.9, 89.4, 89.0, 52.0, 35.6, 31.0; ESI-MS m/z 303.0 (M+Na+).

Provenance & Evidence