Iodoethane → HCID 69693476, compound

Participants

Reaction Steps

To a stirred solution of 1-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]-4-phenyl-1H-imidazole (1.89 g, 5.0 mmol) in tetrahydrofuran (40 mL) was added a solution of 1.5 M n-BuLi in hexane (3.5 mL, 5.5 mmol) at −78° C. over 10 min. After 30 min, a solution of ethyl iodide (2.0 mL, 25.0 mmol) in tetrahydrofuran (10 mL) was added slowly to the mixture at −78° C. The resultant mixture was warmed to room temperature and stirred for 2 h. To the reaction mixture was added water and the volatile components were removed under reduced pressure. 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 10:1 to 6:1) to afford 1.86 g (92%) of the title compound as pale yellow oil: MS (ESI) m/z 379 [M+H]+1H-NMR (CDCl3)δ0.00 (6H, s), 0.88 (9H, s), 1.26 (3H, t, J=7.5 Hz), 2.73 (2H, q, J=7.5 Hz), 2.91 (2H, t, J=6.6 Hz), 3.89 (2H, t, J=6.6 Hz), 7.22-7.28 (4H, m), 7.33-7.41 (4H, m), 7.81 (2H, d, J=7.1 Hz).

Provenance & Evidence