acetic acid; zinc in dichloromethane

1: 83.5 percent / zinc, acetic acid / CH2Cl2 / 20 h / Heating 2: t-butyl-lithium / 1.) THF-n-hexane, -78 deg C 1h; 2.) THF-n-hexane, -78 deg C 30 min 3: 66 percent / toluene-p-sulphonic acid / dioxane; H2O / 0.17 h / 55 °C View Scheme

1: (Me3Si)2NH, pyridine / 16 h / 50 °C 2: 70 percent / BuLi, diisopropylamine / hexane; tetrahydrofuran / 4 h / -60 °C View Scheme

n-butyllithium; N,N-dicyclohexylamine in tetrahydrofuran; hexane T=-78°C; 2 h;