Iodoethane → methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate (2.34 g, 7.17 mmol) in THF (60 mL) and HMPA (15 mL) was added LiHMDS (1 M in THF, 11.0 mL, 11 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 30 min before adding iodoethane (1.23 g, 7.88 mmol). After stirring for another 30 min at 0° C., the mixture was diluted with EtOAc (120 mL) and then quenched with water (20 mL). The organic layer was separated and washed with brine (20 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified via column chromatography (0-15% EtOAc/hexanes) to provide the title compound.

Provenance & Evidence