lithium aluminium tetrahydride in diethyl ether 1 h; Ambient temperature;

n-butyllithium; potassium tert-butylate; diisopropylamine in tetrahydrofuran T=-50°C; 16 h;

lithium diethylamide in N,N,N',N',N'',N''-hexamethylphosphoric triamide; diethyl ether

1: NaBH4 / methanol 2: 62 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h 3: 74.8 percent / n-BuLi / 1.) THF, hexane, -40 deg C, 2.) THF, r.t., 5 h 4: 71 percent / alcoholic 2 N KOH 5: 80 percent / diethyl ether 6: 89 percent / LiAlH4 View Scheme

1: 80 percent / diethyl ether 2: 89 percent / LiAlH4 View Scheme

lithium aluminium tetrahydride in diethyl ether 3 h; Heating; Yield given. Yields of byproduct given;