Imidazole → 4-[1-(tert-Butyldimethylsilyloxy)ethyl]-2-pyridinecarbonitrile

Participants

Reaction Steps

To a solution of 4-[1-(trimethylsilyloxy)ethyl]-2-pyridinecarbonitrile (39.04 g, 0.1624 mol) in THF (200 ml) was added a solution of tetrabutylammonium fluoride in THF (1M, 178.6 ml, 0.1786 mol) at room temperature. After stirring for 0.5 h, the mixture was concentrated. The residue was diluted with ethyl acetate (300 ml) and washed with water (200 ml). The aqueous layer was then extracted with dichloromethane (200 ml×2). The combined organic layers were dried (MgSO4) and concentrated. The residual oil was dissolved in DMF (200 ml). To the solution was added tert-butyldimethylsilylchloride (36.72 g, 0.2436 mol) and imidazole (22.11 g, 0.3248 mol) at room temperture. After stirring for 19 h, diethyl ether (500 ml) and water (200 ml) were added to the mixture and the organic layer was separated. The organic layer was washed with water (100 ml×2), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1:20) to give 39.23 g (92%) of the title compound as an oil.

Provenance & Evidence