Ammonium Chloride → HCID 89262250, compound

Participants

Reaction Conditions

Reaction Steps

The above-mentioned mixture (58.87 g) of 4-(tert-butyldiphenylsilyloxymethyl)-1-(2-fluoroethyl)-1H-imidazole and 5-(tert-butyldiphenylsilyloxymethyl)-1-(2-fluoroethyl)-1H-imidazole was dissolved in THF (1000 mL), and cooled to −78° C. while stirring under nitrogen stream. To the present solution was added dropwise n-butyl lithium (2.76 M hexane solution, 167 mL), followed by stirring at the same temperature for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→65%) using silica gel column (product name: KiloPack 40E, manufactured by Yamazen Corporation) to afford the title compound (18.8 g) and 5-(tert-butyldiphenylsilyloxymethyl)-1-vinyl-1H-imidazole (5.73 g).

Provenance & Evidence