lithium aluminium tetrahydride in tetrahydrofuran 4 h; Heating;

1: 74 percent / 1.) sodium hydride / 1.) mineral oil, THF, r.t., 30 min; 2.) THF, 4 h, reflux 2: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

1: 96 percent / 2,6-di-tert-butyl-p-cresole, Lipase PS / diisopropyl ether; H2O / 1.5 h / Ambient temperature 2: 91 percent / 4-dimethylaminopyridine, pyridine / CH2Cl2 / 15 h / Ambient temperature 3: 93 percent / guanidine / ethanol / 1 h / Ambient temperature 4: 99 percent / pyridine / CH2Cl2 / 40 h / Ambient temperature 5: 88 percent / dimethylsulfoxide / 24 h / 90 °C 6: 1.) aq. 2M-NaOH; 2.) aq. 2M-NaOH / 1.) ETOH, r.t., 18 h; 2.) 3h reflux View Scheme