Acrylonitrile → HCID 18766626, compound

Participants

Reaction Conditions

Reaction Steps

A portion of the above mixture (30 g). was combined with 1,4-diazobicyclo[2.2.2]octane (Aldrich, 3.1 g, 27.7 mmol) and acrylonitrile (20 mL, 304 mmol) and heated at 80° C. for 4 h. The reaction mixture was concentrated in vacuo leaving an oily residue which was dissolved in a tetrahydrofuran/ether mixture (1:1), washed with 10% NaHCO3 (3×100 mL), dried (Na2SO4), and concentrated in vacuo to provide a crude mixture (36.1 g). The separated NaHCO3 layer was extracted with EtOAc (3×50 mL). The combined EtOAc layers were dried (Na2SO4) and concentrated in vacuo to yield 3-cyano-7-hydroxy-2H-1-benzopyran (3.2 g) which was ˜98% pure by 1H NMR.

Provenance & Evidence