Imidazole → (1,1-Dimethyl-2-nitro-ethoxy)-trimethyl-silane

Participants

Reaction Steps

To a solution of nitromethane (100 g, 1.64 mmol) and acetone (5 mL), add a catalytic amount of tetramethylguanidine. Using a syringe pump, add acetone (115 mL, 1.64 mmol) over a period of 72 hours to the stirred solution at RT. Separately, combine chlorotrimethylsilane (206 mL, 1.64 mmol) and imidazole (123 g, 1.8 mmol) at 0° C. Transfer the nitromethane/acetone mixture into the silyl-imidazole mixture and allow this new solution to stir 18 hours at RT. Then cool the reaction to 0° C., dilute with cold ether (450 mL) and wash with cold 1N HCl (200 mL×2). Wash the organic layer with brine (300 mL). Carefully concentrate the crude material in vacuo without heating. Purify by distillation to provide the title compound. Rt=3.85 (GC Initial Temp 100° C.(5 min), 20°/min, Final Temp 180° C. (5 min)).

Provenance & Evidence