Sodium hydride → HCID 21967810, compound

Participants

Reaction Steps

To a solution of methyl 3-acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylate (63, 0.746 g, 2.0 mmol) in THF (10 mL) and MeOH (15 mL) was added sodium hydride (0.240 g of a mineral oil dispersion, 60%, 6.0 mmol) at 0° C. The reaction mixture was stirred for 30 min, and quenched with saturated aqueous NH4Cl 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:EtOAc (3:1, v/v) to afford 0.572 g of 64 (87% yield) mp: 178-179° C.

Provenance & Evidence