sodium hydride in tetrahydrofuran; N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) r.t., 12 h; Yield given;

1: hydrogen bromide 2: alcohol View Scheme

ethanol

1: 100 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature 2: 97 percent / 2,6-di-tert-butyl-4-methylphenol / diisopropyl ether; H2O / 5 h / Ambient temperature; lipase PS (Pseudomonas sp.) 3: 96 percent / pyridine / CH2Cl2 / 21 h / Ambient temperature 4: 88 percent / dimethylsulfoxide / 24 h / 90 °C 5: 100 percent / aq. LiOH / tetrahydrofuran / 17 h / Ambient temperature 6: 93 percent / 2 M NaOH / 2 h / Heating View Scheme

1: lithium alanate 2: acetone; phosphoric acid View Scheme