Uses
3-Trimethylsilylic propionic acid is a carboxylic acid. Carboxylic acids are an important class of organic compounds with wide applications in industry, agriculture, medicine, and daily life. The oxidation reaction from alcohol to acid is a fundamental and important chemical reaction in organic chemistry. In industry and pharmaceuticals, carboxylic acids are often produced through oxidation methods.
Definition
ChEBI: An organosilicon compound that is propionic acid substituted at position 3 by a trimethylsilyl group. It is used as internal reference in the NMR spectrum nuclear magnetic resonance for aqueous solvents (e.g. D2O).
Synthesis
Fe(NO3)3-9H2O (40.5 mg, 0.1 mmol) and DCE (4.0 mL) were added to a 100 mL round-bottomed vial followed by TEMPO (15.7 mg, 0.1 mmol), KCl (7.8 mg, 0.1 mmol), 3-trimethylsilylpropynol (128.6 mg, 1.0 mmol) and DCE ( 1.0 mL). The round-bottomed flask was connected to an air balloon via a pumping valve. The reaction was stirred at room temperature for 48 h until the reaction was monitored for completion by TLC (petroleum ether:ethyl acetate = 5:1). The reaction mixture was filtered through a short column of crude silica gel and drenched with ether (75 mL). After vacuum spin-drying of the solvent, silica gel column chromatography (petroleum ether:ethyl acetate = 5:1) was used for purification to afford 3-trimethylsilylpropynoic acid (92.9 mg, 65%) (petroleum ether:ethyl acetate = 5:1).
