in ethanol T=20°C; 0.5 h;

1: LDA / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) 15 min 2: H2, 2M HCl / Pd/C / ethanol / Ambient temperature 3: 2M HCl / ethanol / 16 h View Scheme

1: H2, 2M HCl / Pd/C / ethanol / Ambient temperature 2: 2M HCl / ethanol / 16 h View Scheme

methyl-magnesium iodide; diethyl ether anschliessend Erwaermen mit Chlorokohlensaeure-aethylester;

sodium ethanolate 0.5 h; Ambient temperature;

1: hydrazine hydrate; sodium ethylate solution / 170 - 175 °C 2: methyl magnesium iodide; diethyl ether / anschliessend Erwaermen mit Chlorokohlensaeure-aethylester View Scheme

1: 55 percent / 70percent HNO3 / 2 h / 30 °C 2: 77 percent / KOH / ethanol / 18 h / 0 °C 3: 70 percent / hexadecyl(tributyl)phosphonium bromide / acetonitrile / 24 h / Ambient temperature 4: 85 percent / 2 M aq. NaOH / ethanol / Heating View Scheme