Triethylamine → 4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxy methyl)-1H-imidazole

Participants

Reaction Steps

1-(2-Trimethylsilylethoxymethyl)-1H-imidazole-4-methanol (100 g, WO 01/02145) was dissolved in dichloromethane (1 L), and triethylamine (hereinafter sometimes referred to as TEA) (122 mL), 4-(N,N-dimethylamino)pyridine (hereinafter sometimes referred to as DMAP) (5.35 g) and tert-butyldiphenylsilyl chloride (hereinafter sometimes referred to as TBDPSCl) (149 mL) were added under stirring. After stirring for a day, the reaction mixture was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%→50%) using a silica gel column (trade name: Ultrapack E, manufactured by Yamazen Corporation) to give the title compound (146 g).

Provenance & Evidence