1: 40 percent / NaI / acetone / 10 h / Heating 2: 1.) LDA / 1.) THF, 0 deg C, 1 h; 2.) r.t., 2 h 3: 70 percent / 50percent aq.NaOH / 2 h / Heating View Scheme

lithium diisopropyl amide 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 3 h; Multistep reaction;

1: NaI / acetone / Ambient temperature 2: 1.) NaH, 2.) N-butyllithium 3: 1.) NaH / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT 4: MeCu / tetrahydrofuran / 3 h / -25 °C 5: DIBAL / diethyl ether; hexane / 2 h / 0 °C View Scheme

1: NaI / acetone / Ambient temperature 2: 1.) NaH, 2.) N-butyllithium View Scheme

n-butyllithium; sodium hydride Yield given. Multistep reaction;

1: 2-methyl-4-hydroxy-1-butene With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in diethyl ether; hexane T=20°C; 6 h; 2: TsOCH2CH2CH(CH3)=CH2 in diethyl ether T=-78 - 20°C;

1: 15 percent 2: NaH 3: dimethyl copper lithium 4: 1,2-dimethylimidazole / diethyl ether / 3 h / Ambient temperature; Irradiation; without base, other solvents View Scheme

1: 1.) n-butyllithium, diisopropylamine / 1.) THF, 0 deg C, 0.5 h, 2.) room temperature 2: lithium aluminum hydride / diethyl ether / 1.75 h / Ambient temperature 3: 90 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

1: 1.) n-butyllithium, diisopropylamine / 1.) THF, 0 deg C, 0.5 h, 2.) room temperature 2: lithium aluminum hydride / diethyl ether / 1.75 h / Ambient temperature 3: 90 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 2.5 h / Ambient temperature 4: 1.) n-butyllithium / 1.) THF, 0 deg C (0.5 h), -> room temperature (0.25 h), 2.) 0 deg C, 1.5 h View Scheme

sodium iodide in acetone 24 h;