HCID 23003163, compound → HCID 23003162, compound

Participants

Reaction Conditions

Reaction Steps

To a flame dried flask was added a solution of 4-[5-(2,6-dichlorobenzyloxy)-3-formyl-indol-1-yl]butyronitrile (0.23 g, 0.59 mmol) in THF (10 mL) and cooled to −78° C. To this solution ethyl magnesium bromide (1.0M in THF, 0.65 mL, 0.65 mmol) was added via dropwise addition. The reaction was stirred at −78° C. for 3 h then warmed to room temperature slowly. After stirring at room temperature for 18 h, the reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over Na2SO4. Purification by flash column chromatography (silica gel, ethyl acetate/hexane) afforded three products, one of which was identified by NMR, IR and LC-MS as the ketone 4-[5-( 2,6-dichlorobenzyloxy)-3-propionyl-indol-1-yl]butyronitrile (0.034 g, 14%). MS(ES) m/e 415.0 [M+H]+. None of the expected secondary alcohol was recovered.

Provenance & Evidence