1: 85 percent / I2, Ph3P, imidazole / acetonitrile 2: EtMgBr 3: conc. HCl / methanol / Ambient temperature 4: I2, Ph3P, imidazole / acetonitrile 5: EtMgBr 6: conc. HCl / methanol / Ambient temperature View Scheme

1: 1) BuLi / 1) THF, HMPA 2: conc. HCl / methanol / Ambient temperature 3: 85 percent / I2, Ph3P, imidazole / acetonitrile 4: EtMgBr 5: conc. HCl / methanol / Ambient temperature 6: I2, Ph3P, imidazole / acetonitrile 7: EtMgBr 8: conc. HCl / methanol / Ambient temperature View Scheme

1: EtMgBr 2: conc. HCl / methanol / Ambient temperature 3: I2, Ph3P, imidazole / acetonitrile 4: EtMgBr 5: conc. HCl / methanol / Ambient temperature View Scheme

1: I2, Ph3P, imidazole / acetonitrile 2: EtMgBr 3: conc. HCl / methanol / Ambient temperature View Scheme

hydrogenchloride in methanol 1 h; Yield given;

1: 1.) EtMgBr, 2.) CuCl / 1.) THF, 20 deg C, 2 h, 2.) THF, 20 deg C, 24 h 2: 1.2 N HCl / methanol / 1 h View Scheme

ethylmagnesium bromide

1: H2, quinoline / Lindlar catalyst / ethanol 2: MnO2 / CH2Cl2 / 24 h / 20 °C 3: 1.) BuLi / 1.) THF, hexane, 2.) THF, hexane, 20 deg C, 4 h View Scheme