Uses
2-(Trimethylsilyl)thiazole is used as formyl anion equivalent; effective one-carbon homologating reagent of alkoxy aldehydes, amino aldehydes, and
dialdoses.It takes part in the reactions of Homologation of Aldehydes, Metalation and Reactivity with Electrophiles, Cross-coupling Reactions, etc.
Synthesis
A solution of thiazole (5.03 g) dissolved in ether (59 mL) was slowly added dropwise to a mixture of n-butyllithium (2.5 M hexane solution, 24 mL) and ether (18 mL) at -78 °C. After completion of the dropwise addition, the reaction was kept at -78°C for 30 min. Subsequently, a solution of trimethylchlorosilane (TMSCl, 6.41 g) dissolved in ether (59 mL) was added at the same temperature. The reaction mixture was continued to be stirred at -78 °C for 1 h, followed by slow warming to room temperature. After completion of the reaction, the reaction mixture was washed with saturated sodium bicarbonate (NaHCO3) solution and the organic phase was dried with anhydrous sodium sulfate (Na2SO4). After removal of the solvent by decompression evaporation, the residue was subjected to decompression distillation (80 °C/14 mmHg) to afford the target product 2-(trimethylsilyl)thiazole (I-54) in 90% yield. The product was analyzed by GC-MS and showed the molecular ion peak (M+H)+ with m/z of 157.10.
References
[1] Patent: WO2011/79114, 2011, A1. Location in patent: Page/Page column 125
[2] Patent: WO2012/48129, 2012, A2. Location in patent: Page/Page column 385
[3] Tetrahedron Letters, 2008, vol. 49, # 1, p. 66 - 69
[4] Journal of Organic Chemistry, 1988, vol. 53, # 8, p. 1748 - 1761
[5] Patent: WO2009/21992, 2009, A2. Location in patent: Page/Page column 84
