in diethyl ether; ethyl acetate

methanol; lithium hydroxide; water in tetrahydrofuran T=20°C; 1 h;

in tetrahydrofuran; methanol

lithium diisopropyl amide 1.) THF, -78 deg C, 25 min, 2.) -78 deg C --> room temperature, overnight; Yield given. Multistep reaction. Yields of byproduct given;

1: 93 percent / LiAlH4 / diethyl ether / 4 h / Heating 2: 90 percent / pyridine / CHCl3 / 0 °C View Scheme

1: 89 percent / N,N,N',N'-tetramethylethylenediamine / 12 h / 200 °C 2: 100 percent / camphorsulfonic acid (CSA) / benzene / 12 h / Heating 3: 1.) sec-BuLi / 1.) THF, -78 deg C 4: 35 percent / NaH / dimethylsulfoxide / 24 h / 22 °C 5: H2 / 10percent Pd/C / dioxane / 0.75 h / 22 °C / 760 Torr 6: camphorsulfonic acid (CSA) / CH2Cl2; tetrahydrofuran / 5 h / 0 °C 7: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) a) 30 min, b) 0 deg C, 1 h 8: 58 percent / camphorsulfonic acid (CSA) / methanol; benzene / 0.33 h / Heating View Scheme