1: 96 percent / KOH / diethyl ether / 1.)<0 deg C, 2.)30 min., 0 deg C 2: 1.)Ethylmagnesium bromide, 2.)CuBr 3: 2.15 g / H2 / P-2 nickel / 4 h 4: 0.55 g / AcOH, H2O / tetrahydrofuran / 16 h / 20 °C View Scheme

1: 96 percent / KOH / diethyl ether / 1.)<0 deg C, 2.)30 min., 0 deg C 2: 1.)Ethylmagnesium bromide, 2.)CuBr 3: 2.15 g / H2 / P-2 nickel / 4 h 4: 0.55 g / AcOH, H2O / tetrahydrofuran / 16 h / 20 °C 5: 47 percent / 2-Chloro-1-methylpyridinium iodide, Triethylamine / acetonitrile / Heating View Scheme