Tetrabutylammonium Fluoride → HCID 69475822, compound

Participants

Reaction Steps

To a solution of compound 2 (0.64 g, 0.92 mmol) in 10.0 mL of anhydrous THF was added TBAF (1.20 mL, 1.0 M in THF) at 0° C. The resulting solution was stirred for 6 h at rt. The solvent was removed under reduced pressure and the residue was purified on silica gel column chromatography (Hexane:EtOAc=4:1 to 1:1 v/v) to give compound 3 (0.39 g, 0.85 mmol) in 93% yield. 1H NMR (CD3OD, 400 MHz) δ 8.58 (d, J=7.6, 1H), 8.00 (m, 4H), 7.63 (m, 3H), 7.51 (m, 4H), 6.16 (dd, J=17.6, 1.6, 1H), 5.55 (dd, J=4.4, 1.6, 0.5H), 5.47 (m, 1H), 5.42 (dd, J=4.4, 1.6, 0.5H), 4.51 (m, 1H), 4.06 (dd, J=12.8, 2.4, 1H), 3.86 (dd, J=12.8, 3.2, 1H); MS calcd for C23H20FN3O6 m/z 454.1 (M+H)+, found 454.2.

Provenance & Evidence