87630-35-1

1-(Triisopropylsilyl)pyrrole may be employed as reagent in perfluoroalkylation and Vilsmeier formylation reactions. It may be used in the preparation of ethyl 2-(2,4-dinitrophenylhydrazono]-3-[ 1-(triisopropylsily1)-pyrrol-2-yflpropanoate; heterocyclic base, 3-nitropyrrole and 3-nitropyrrole, required for the synthesis of 1 -(2?-deoxy-β-D-ribofuranosyl)-3-nitropyrrole. It participates in various electrophilic substitution reactions specifically at β-position, via reaction with various electrophilic reagents (Br+, I+,NO2+,etc).

At -78 °C, n-butyllithium (n-BuLi, 1.57 M in n-hexane, 17.3 mL, 27.1 mmol) was slowly added dropwise to a solution of tetrahydrofuran (THF, 36 mL) of pyrrole (1.52 g, 22.6 mmol), and the reaction mixture was kept stirring at -78 °C for 30 min. Subsequently, triisopropylchlorosilane (TIPSCl, 5.3 mL, 24.9 mmol) was added to the reaction mixture and stirring was continued at -78 °C for 5 hours. Upon completion of the reaction, the reaction was quenched by addition of saturated aqueous ammonium chloride (NH4Cl) to the mixture at 0 °C and the mixture was extracted with ethyl acetate (AcOEt). The organic phases were combined and concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was purified by silica gel (SiO2) column chromatography (eluent: n-hexane/ethyl acetate=10:1) to afford 1-(triisopropylmethylsilyl)pyrrole (4.94 g, 98% yield) as a colorless oil.

[1] Journal of Natural Products, 2004, vol. 67, # 11, p. 1929 - 1931
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4358 - 4361
[3] Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5504 - 5508
[4] Chemistry - An Asian Journal, 2016, vol. 11, # 7, p. 986 - 990
[5] Tetrahedron, 2008, vol. 64, # 49, p. 11180 - 11184