sodium hydroxide in methanol; water T=25 - 27°C; 16 h;

1: 52 percent / lithium tetrahydridoaluminate / diethyl ether / 2 h / Heating 2: 2.) Et3N / 1.) toluene, reflux, 1 h, 2.) toluene, reflux, 21 h 3: 18 percent / NaOH / H2O; methanol / 16 h / 25 - 27 °C View Scheme

1: 2.) Et3N / 1.) toluene, reflux, 1 h, 2.) toluene, reflux, 21 h 2: 18 percent / NaOH / H2O; methanol / 16 h / 25 - 27 °C View Scheme

1: 1.) butyllithium, diisopropylamine, 2.) HMPA / 1.) hexane, THF, - 78 deg C, 20 min, 2.) hexane, THF, - 78 deg C, 45 min 2: 52 percent / lithium tetrahydridoaluminate / diethyl ether / 2 h / Heating 3: 2.) Et3N / 1.) toluene, reflux, 1 h, 2.) toluene, reflux, 21 h 4: 18 percent / NaOH / H2O; methanol / 16 h / 25 - 27 °C View Scheme