dichloro bis(acetonitrile) palladium(II); copper(l) iodide in acetonitrile Inert atmosphere;

CuI in n-heptane; 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran; ethyl acetate; acetonitrile

1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0 - 20 °C 3: hydrogen / 5 palladium on charcoal / tetrahydrofuran / 96 h / 50 °C / 2250.23 - 3000.3 Torr / autoclave; Inert atmosphere View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1.1: hydrogen / Isopropyl acetate / 30 &deg;C / 750.08 Torr / |Inert atmosphere; |Molecular sieve<br />2.1: sodium hydrogencarbonate / ethyl acetate / 20 &deg;C / |Inert atmosphere<br />2.2: 80 &deg;C / |Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: sodium hydrogencarbonate / ethyl acetate<br />2.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale<br />2.2: 16 h / 80 &deg;C / |Large scale<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: magnesium / tetrahydrofuran / 3.5 h / |Inert atmosphere<br />1.2: 16 h / 25 &deg;C<br />2.1: potassium hydroxide / methanol / 25 &deg;C<br />3.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale<br />3.2: 16 h / 80 &deg;C / |Large scale<br /> <br /> &nbsp;