Imidazole → Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

Participants

Reaction Steps

To a solution of methyl 4-hydroxycyclohexane-carboxylate (a cis/trans mixture, 5.00 g, 31.6 mmol) and imidazole (4.30 g, 63.2 mmol) in dimethylformamide (20 ml) was added t-butyldimethylsilyl chloride (5.72 g, 37.9 mmol) at room temperature, and stirred at the same temperature for 5 hours. After completion of the reaction, an ethyl acetate/toluene (1/1) solution and water were added thereto, and the organic layer was collected, dried over sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexane-carboxylate (8.66 g, 100%) was obtained.

Provenance & Evidence