lithium iodide in N,N-dimethyl-formamide T=150°C; 4 h;

1: sodium hydroxide / H2O; methanol / 2 h / Heating 2: quinoline / Heating View Scheme

in tetrahydrofuran T=-30°C; 1 h;

1: 84 percent / pyridine, piperidine / 3 h / 120 °C 2: 71 percent / sodium borohydride / methanol / 1.) 5 deg C, 15 min, 2.) 20 deg C, 0.5 h 3: 1.82 g / TsOH*Py / acetone; H2O / 2 h / Heating 4: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.)a) THF, hexane, -78 deg C, 1 h, b) 20 deg C, 15 h View Scheme

1: 84 percent / pyridine, piperidine / 3 h / 120 °C 2: 71 percent / sodium borohydride / methanol / 1.) 5 deg C, 15 min, 2.) 20 deg C, 0.5 h 3: 1.82 g / TsOH*Py / acetone; H2O / 2 h / Heating 4: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.)a) THF, hexane, -78 deg C, 1 h, b) 20 deg C, 15 h View Scheme

sodium

n-butyllithium 1.) THF, hexane, -78 deg C, 1 h, 2.)a) THF, hexane, -78 deg C, 1 h, b) 20 deg C, 15 h; Yield given. Multistep reaction;

sodium ethanolate in tert-butyl alcohol 48 h; Ambient temperature;

1: sodium hydroxide / H2O; methanol / 2 h / Heating 2: quinoline / Heating 3: thionyl chloride / dimethylformamide / 1 h / 30 °C 4: 1 h / 20 °C View Scheme