Pyrrole → N-Triisopropylsilylpyrrole

Participants

Reaction Conditions

Reaction Steps

Pyrrole (1.0 mL, 0.96 g, 15 mmol) was added dropwise at 0° C. to a stirred suspension of sodium hydride (0.758 g of 50% dispersion in mineral oil, 16 mmol) in anhydrous DMF (20 mL). When hydrogen evolution (foaming) had ceased, triisopropylsilyl chloride (3.1 mL, 2.8 g, 15 mmol) was added dropwise and stirring at 0° C. was then continued for 0.75 h. The reaction mixture was partitioned between ether and water, and the ether phase was washed with water, dried oversodium sulfate, and evaporated in vacuum. Purification by column chromatography on silica gel (hexane/ethyl acetate=10:1) gave an oil (1.01 g, 30.2% yield); 1H NMR (CDCl3) δ 1.09 (d, 18 H, Me), 1.45 (sept, 3 H, CH), 6.31 (t, 2H, H-3.4), 6.80 (t, 2H, H-2.5). MS (M+H) m/z 224.

Provenance & Evidence