1: 1.) n-BuLi / 1.) hexane, THF, ether, -78 deg C, 30 min, 2.) hexane, THF, ether, from -78 to 23 deg C, 2 h 2: 97 percent / CeCl3*7H2O, NaBH4 / methanol / 0.75 h / 0 °C View Scheme

1: With lithium aluminium tetrahydride in diethyl ether T=0°C; 0.5 h; Inert atmosphere; 2: With hydrogenchloride in diethyl ether; water T=0 - 20°C; Inert atmosphere;

1.1: 53 percent / LiHMDS / tetrahydrofuran / -78 - -20 °C 2.1: tetrahydrofuran / 0.75 h / 0 °C 2.2: 40 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C View Scheme

in tetrahydrofuran 1) 0.5 h, -78 deg C, 1 h, RT;

1: 82 percent / tetrahydrofuran / 1) 0.5 h, -78 deg C, 1 h, RT 2: 93 percent / 2N aq. KF / benzyltriethylammonium chloride / tetrahydrofuran / 3 h View Scheme

sulfuric acid; water ether 1a) overnight, RT, 1b) 3 h, reflux, 2a) 1 h, RT, 2b) 1h, RT; Yield given. Multistep reaction;

1: 3-(2-methylpropoxy)cyclohex-2-en-1-one With lithium diisopropyl amide in tetrahydrofuran T=-78 - 20°C; 2: benzyl bromide in tetrahydrofuran T=-78 - 20°C; Further stages.;

1: in tetrahydrofuran; diethyl ether T=20°C; 0.5 h; 2: With sulfuric acid in tetrahydrofuran; diethyl ether; water

1.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 88 percent / tetrahydrofuran; hexane / 4 h / -78 - 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: 90 percent / tetrahydrofuran; hexane / 1 h 3.1: 94 percent / PPTS / benzene / 1.5 h / Heating 4.1: LiAlH4 / tetrahydrofuran / 0.17 h / 0 °C 4.2: 76 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C 5.1: BF3*Et2O; ethylene glycol / CH2Cl2 / 20 °C 5.2: 75 percent / aq. HCl / tetrahydrofuran / 24 h View Scheme

1.1: diethyl ether / 0.5 h / 20 °C 1.2: 3.1 g / H2SO4 / H2O; diethyl ether 2.1: 3.1 g / hydrogen / Pd/C View Scheme