Imidazole → 4-Tert-butyl(dimethyl)silyloxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To a solution of 0.220 g (0.940 mmol) of 4-hydroxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester in 5 mL of DMF was added 0.156 g (1.034 mmol) of t-butyldimethylsilyl chloride and 0.160 g (2.350 mmol) of imidazole and the reaction was stirred at room temperature for 14 h. The reaction mixture was diluted with water and extracted with ether. The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 0.315 g of 4-tert-butyl(dimethyl)silyloxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester.

Provenance & Evidence