Tetrabutylammonium Fluoride → 2-(1H-pyrrol-3-yl)pyridine

Participants

Reaction Steps

To a solution of 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]pyridine (1 g, 3.2 mmol) in anhydrous THF (15 mL) was added TBAF (3.84 mL of a 1M solution in THF, 3.84 mmol). After stirring for 10 min. at rt, the reaction was complete. The reaction mixture quenched with H2O (40 mL), extracted with EtOAc (3×25 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and chromatographed on silica gel eluting with EtOAc:hexane (1:1) to afford 2-(1H-pyrrol-3-yl)pyridine as a solid. 1H NMR (CD3Cl, 300 MHz) δ 8.55 (ddd, 1H), 7.65 (dt, 1H), 7.54 (dd, 1H), 7.46˜7.43 (d, 1H), 7.07 (ddd, 1H), 6.85 (dd, 1H), 6.74 (dd, 1H). MS (ESI) 145.1 (M++H).

Provenance & Evidence