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3-(Trimethylsilyl)propiolic acid may be used in the regioselective preparation of 1,5-trisubstituted 1H-1,2,3-triazoles. It is also used as pharmaceutical intermediate.

The general procedure for the synthesis of 3-(trimethylsilyl)propynoic acid from 3-trimethylsilylpropynal was as follows: in a reaction test tube, trans-2-decene (167 mg, 1.0 mmol) was added to a mixture containing Fe(NO3)3-9H2O (4.1 mg, 0.010 mmol) and CF3COONa (28 mg, 0.20 mmol) in an EtOAc (0.50 mL) in suspension. An O2 balloon (1 atm) was attached to the top of the test tube to displace the internal atmosphere with O2. After the reaction mixture was stirred at 25 °C for 16 h, EtOAc (3 mL) and 1 M HCl aqueous solution (1 mL) were added and the resulting two-phase mixture was stirred for 1 min. The organic phase was separated and the aqueous phase was extracted with EtOAc (3 mL × 2). After combining the organic phases, quantitative biphenyl (as an internal standard for NMR analysis) was added. The conversion of the substrate and the yield of the product were determined by NMR analysis (400 MHz, CDCl3, 25 °C). Products were identified by comparing the NMR signals of real samples. Each reaction was repeated twice to ensure reproducible results.

[1] Chemistry Letters, 2016, vol. 45, # 2, p. 188 - 190