Dichloromethane → 3-Acetoxyestra-1,3,5(10)-trien-17-one-2-carboxaldehyde

Participants

Reaction Steps

To a solution of 3-hydroxyestra-1,3,5(10)-trien-17-one-2-carboxaldehyde (60, 1.92 g, 6.43 mmol) of CH2Cl2 (30 mL) was added triethylamine (2.3 mL, 16 mmol) and acetic anhydride (0.94 mL, 9.6 mmol) at room temperature. The reaction mixture was stirred for 16 h, H2O was added, and the mixture was 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:EtOAc (2:1→3:2, v/v) to afford 2.08 g of 61 (95% yield) mp: 179-181° C.

Provenance & Evidence