pyridine; thionyl chloride in toluene 12 h; Heating;

1: 99 percent / H2SO4 / 12 h / Heating 2: 94 percent / LiAlH4 / tetrahydrofuran / 12 h / 20 °C 3: 96 percent / SOCl2; pyridine / toluene / 12 h / Heating View Scheme

1: 94 percent / LiAlH4 / tetrahydrofuran / 12 h / 20 °C 2: 96 percent / SOCl2; pyridine / toluene / 12 h / Heating View Scheme

1: 86 percent / lithium aluminum hydride / diethyl ether / 1 h / Heating 2: 87 percent / thionyl chloride; pyridine / 1 h / Heating View Scheme

potassium hydroxide; borane-THF 1) THF, 2) THF, MeOH, Pt-anode, 10 mA/cm-2, 52.8 mF, 28 V, 5 deg C; 1)THF, 2) 1 M tBuOK, tBuOH, MeCN, THF, Pt-anode, 10 mA/cm-2, 250 V; Yield given. Multistep reaction;