Tetrabutylammonium Fluoride → 2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-ylamine

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Reaction Steps

[2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester (681 mg, 1.39 mmol) was treated with a 1 M solution of TBAF in THF (2.78 mL). The resulting solution was stirred at rt overnight, then quenched with glacial acetic acid (0.155 mL). The solution was passed through a short plug of silica gel, eluting with toluene and concentrated in vacuo to afford 2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-ylamine (299 mg, 80% for two steps) as a creamy white solid: 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 1.36 (s, 18H), 4.60 (s, 2H), 6.24 (s, 2H), 7.46 (d, 4H, J=8.7 Hz), 7.52 (d, 4H, J=8.7 Hz).

Provenance & Evidence