Acrylonitrile → 9-methoxy-3H-benzo[f]chromene-2-carbonitrile

Participants

Reaction Steps

Under an anhydrous atmosphere, the aldehyde obtained in Step C (2 g:9.9 mmol) is partially solubilized in acrylonitrile (6.5 ml:49.4 mmol:10 eq.). The solution becomes clear after the addition of 1,4-diazabicyclo[2.2.2]octane (227 mg:2.47 mmol:0.25 eq.) and becomes a red colour when heated at reflux for a period of 18 hours. The reaction medium is then diluted with ethyl acetate and washed in succession with a 1N sodium hydroxide solution (20 ml) and then a 1N hydrochloric acid solution (20 ml). The concentrated organic phases are purified on a flash silica column eluted with an AcOEt/PE mixture (0.1/1).

Provenance & Evidence