Imidazole → HCID 69334501, compound

Participants

Reaction Steps

To a solution of 3-benzyloxyestra-1,3,5(10)-trien-17α-ol (49, 1.45 g, 4.0 mmol) in DMF (5.0 mL) were added imidazole (0.408 g, 6.0 mmol) and tert-butyldimethylchlorosilane (0.784 g, 5.2 mmol) at room temperature. The reaction mixture was stirred for 2 h, and quenched with saturated aqueous NaHCO3 at 0° C., and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:CHCl3 :EtOAc (50:50:1→20:20:1, v/v) to afford 1.91 g of 50 (100% yield).

Provenance & Evidence