Water → Methyl 3-(4-Ethynylphenyl)propanoate

Participants

Reaction Steps

Methyl 3-(4-((trimethylsilyl)ethynyl)phenyl)propanoate (225 mg, 0.86 mmol) and potassium carbonate (234 mg, 1.69 mmol) was dissolved in MeOH (9 mL) and stirred vigorously for 2½ hours at room temperature. The reaction was added water and extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4 before concentrated under vacuum to give 138 mg (90%) of a brown, oily product. Rf: 0.31 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.43-7.40 (m, 2H), 7.17-7.14 (m, 2H), 3.66 (s, 3H), 3.04 (s, 1H), 2.97-2.92 (t, 2H, J=7.7 Hz), 2.65-2.59 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 141.4, 132.3, 128.3, 120.2, 83.5, 76.8, 51.6, 35.3, 30.8; ESI-MS m/z 287.1 (MNa+).

Provenance & Evidence