Tert-Butyl nitrite → Methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-cyanomethoxy-acrylate

Participants

Reaction Steps

A solution of 34.3 g (300 mmol) of t-butyl nitrite and 25 g (100 mmol) of methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-acrylate in 30 ml of t-butanol is added dropwise to a solution of 12.3 g (110 mmol) of potassium t-butoxide in 120 ml of t-butanol, and the reaction solution warms to 45° C. After 2 hours, 13.2 g (110 mmol) of bromoacetonitrile are added to this mixture and stirring is continued at 20° C. for a further 18 hours. The reaction mixture is concentrated under reduced pressure, taken up in methyl t-butyl ether, washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed over silica gel using hexane/acetone (8:2). 14.9 g (46.9% of theory) of methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-cyanomethoxy-acrylate are obtained.

Provenance & Evidence