Butanal → HCID 12411552, compound

Participants

Reaction Steps

10.7 g (148 mmol) of butanal was added gradually to 300 ml of a solution of 11.6 g of indole (98.6 mmol) and 14.2 g of Meldrum's acid (98.6 mmol) in acetonitrile at room temperature. 500 mg of proline was added to the reaction mixture which was then stirred overnight. The solvent was removed by evaporation under reduced pressure. The residue was dissolved in 200 ml of pyridine, and 15 ml of ethanol and 2.5 g of copper powder were added to the resulting solution. The reaction mixture was then refluxed for 4 hours and the copper powder was filtered off after this time. The solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 15% v/v solution of ethyl acetate in hexane) to yield 20.1 g (78%) of the title compound as an oil.

Provenance & Evidence