potassium hydroxide; hydrazine hydrate in ethylene glycol 1.5 h; Heating;

1: 81 percent / TiCl4 / CH2Cl2 / 1) -70 deg C, 2) -20 deg C, 2 h 2: 92 percent / ethyl orthoformate / p-TsOH*H2O / 5 h / Heating 3: 98 percent / KOH, NH2NH2*H2O / ethane-1,2-diol / 1.5 h / Heating View Scheme

1: 92 percent / ethyl orthoformate / p-TsOH*H2O / 5 h / Heating 2: 98 percent / KOH, NH2NH2*H2O / ethane-1,2-diol / 1.5 h / Heating View Scheme

1: 1) n-butyllithium, diisopropylamine / 1) THF, hexane, -70 deg C, 1 h, 2) -70 deg C, 1 h 2: 81 percent / TiCl4 / CH2Cl2 / 1) -70 deg C, 2) -20 deg C, 2 h 3: 92 percent / ethyl orthoformate / p-TsOH*H2O / 5 h / Heating 4: 98 percent / KOH, NH2NH2*H2O / ethane-1,2-diol / 1.5 h / Heating View Scheme

1: 1) NaH / 1) DMF, 1 h, 0 deg C, 2) a) 2 h, 0 deg C, b) RT 2: 3.6 percent / conc. HCl / 2 h / Ambient temperature View Scheme

1: 1) NaH / 1) DMF, 1 h, 0 deg C, 2) a) 2 h, 0 deg C, b) RT 2: 45 percent / conc. HCl / 2 h / Ambient temperature 3: 50 percent / NaOH / H2O / 1 h / Heating View Scheme