Reaktion #515336

Reaktionsgleichung

aldehyde

2-Hydroxy-7-methoxy-1-naphthaldehyde

acrylonitrile

1,4-diazabicyclo[2.2.2]octane

→

9-Methoxy-3H-benzo[f]chromene-2-carbonitrile

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux for a period of 18 hours
3. 3
   Waschenwashed in succession with a 1N sodium hydroxide solution (20 ml)
4. 4
   SonstigeThe concentrated organic phases are purified on a flash silica column
5. 5
   Wascheneluted with an AcOEt/PE mixture (0.1/1)

Vorschrift

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).

Quelle