Trimethylsilylacetylene → Methyl 3-[4-[(Trimethylsilyl)ethynyl]phenyl]propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (250 mg, 0.86 mmol) and trimethylsilylacetylene (0.22 mL, 1.70 mmol) according to the general procedure IA. After filtration through Celite, the product was obtained as a brown oil and used without purification in the next step. Rf: 0.38 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.39-7.37 (m, 2H), 7.13-7.11 (m, 2H), 3.65 (s, 3H), 2.96-2.91 (t, 2H, J=7.6 Hz), 2.63-2.58 (t, 2H, J=7.8 Hz), 0.24 (s, 9H); 13CNMR (CDCl3) δ 173.1, 141.1, 132.1, 128.2, 121.1, 105.0, 93.8, 51.6, 35.6, 30.8, 0.0.

Provenance & Evidence