Tetrabutylammonium Fluoride → HCID 22291371, compound

Participants

Reaction Steps

To a stirred solution of 1-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]-2-ethyl-4-phenyl-1H-imidazole (1.84 g, 4.6 mmol) in tetrahydrofuran (25 mL) was added tetrabutylammonium fluoride (1.84 g, 6.9 mmol) at 0° C. After 1 h, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 0:1) to afford 1.44 g (quant) of the title compound as colorless amorphous : MS (ESI) m/z 293 [M+H]+1H-NMR (CDCl3)δ1.26 (3H, t, J=7.5 Hz), 2.72 (2H, q, J=7.5 Hz), 2.95 (2H, t, J=6.6 Hz), 3.93 (2H, t, J=6.6 Hz), 7.22-7.28 (4H, m), 7.34-7.41 (4H, m), 7.79 (2H, d, J=7.1 Hz).

Provenance & Evidence