Imidazole → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

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Reaction Steps

Under nitrogen atmosphere, an N,N-dimethylformamide (33 ml) solution of tert-butylchlorodiphenylsilane (8.78 g, 32.0 mmol) was dropwise added at room temperature to an N,N-dimethylformamide (100 ml) solution of N-methylethanolamine (2.00 g, 26.6 mmol) and imidazole (2.72 g, 39.9 mmol), and stirred for 5.5 hours. The solvent was evaporated away under reduced pressure, then the residue was dissolved in ethyl acetate, and the solution was washed with saturated sodium hydrogencarbonate water, water and saturated brine. Next, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate gave the entitled compound (3.21 g, 39%) as a pale yellow oil.

Provenance & Evidence