Methanol → HCID 21967809, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylic acid (62, 1.07 g, 3.0 mmol) in dichloroethane (10 mL) was added thionyl chloride (0.28 mL, 3.9 mmol) and DMF (1 drop) at room temperature. The reaction mixture was stirred for 30 min at 80° C. After the reaction mixture was cooled to 0° C., MeOH (5.0 mL) and triethylamine (1.0 mL) were added, and stirred for 1 h. The reaction mixture was diluted with EtOAc and 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:EtOAc (3:1→3:2, v/v) to afford 0.764 g of 63 (69% yield) mp: 182-183° C.

Provenance & Evidence