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

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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 h. to the stirred solution at RT. In a separate flask, combine chlorotrimethylsilane (206 mL, 1.64 mmol) and imidazole (123 g, 1.8 mmol) at 0° C. Transfer the nitromethane/acetone solution into the trimethylsilyl-imidazole mixture and allow the resulting mixture to stir 18 h 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. 1H NMR (300 MHz, CDCl3) δ 4.20 (s, 2H), 1.28 (s, 6H), 0.01 (s, 9H).

Provenance & Evidence