Imidazole → HCID 58250168, compound

Participants

Reaction Steps

1-Bromododecanol (2.511 g, 9.47 mmol), tert-butyldiphenylsilylchloride (2.66 mL, 15.15 mmol), and imidazole (1.418 g, 20.83 mmol) were dissolved in dry DMF (20 mL) and the resulting mixture was stirred under nitrogen for 3 h at room temperature. Upon completion of reaction, water (15 mL) and diethyl ether (25 mL) were added, the two layers were separated and the water layer was extracted with diethyl ether (3×25 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and filtrate evaporated. The crude was purified by silica gel column chromatography using 100% hexane to 5% ethyl acetate/hexane as eluent to afford the title product as a clear thick oil (3.57 g, 75%). 1H NMR (CDCl3): δ7.66 (m, 4H), 7.39 (m, 6H), 3.62 (t, 2H, J=6.5 Hz), 3.40 (t, 2H, J=6.9 Hz), 1.85 (m, 2H), 1.54 (m, 2H), 1.44-1.25 (m, 16H), 1.04 (s, 9H). m/z (APCI) 505.37 (M++1).

Provenance & Evidence