18-crown-6 ether in water; ethyl acetate T=50°C; 14 h;

1: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 2: 1.) n-BuLi / 1.) n-hexane, THF, -78 degC, 30 min; 2.) THF, -78 degC, 2 h View Scheme

1: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 2: 1.) n-BuLi / 1.) n-hexane, THF, -78 degC, 30 min; 2.) THF, -78 degC, 2 h 3: 65 percent / Raney-Ni / ethanol / 5 h / Heating View Scheme

1: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 2: 1.) n-BuLi 3: 28 percent / Raney-Ni / ethanol / 12 h / Heating 4: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme