Imidazole → HCID 57046043, compound

Participants

Reaction Steps

A solution of 25 (8.04 g, 27.5 mmol) and imidazole (7.05 g, 103.55 mmol) in anhydrous DMF (80 ml) was treated with tert-butyldimethylsilyl chloride (6.70 g, 44.45 mmol). The mixture was stirred at room temperature under a blanket of argon for 40 min and quenched by the addition of water (100 ml). The reaction mixture was extracted with ethyl acetate (3×100 ml), and the combined organic extract was washed with brine (2×100 ml) and dried over Na2SO4. The solvent was evaporated and the product purified by flash column chromatography over silica gel to give 9.77 g (87.4%) of pure 26 as an oil. Analysis calculated for C23H38O4Si.0.5 H2O: C, 66.46; H, 9.46. Found: C, 66.41; H, 9.31.

Provenance & Evidence