1: 71 percent / NaOAc, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 25 deg C, 16 h 2: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 3: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 4: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 5: 1.) t-BuLi, 2.) CH3OH / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, - 85 deg C View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 1.) t-BuLi, 2.) CH3OH / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, - 85 deg C View Scheme

1: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 2: 1.) t-BuLi, 2.) CH3OH / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, - 85 deg C View Scheme

1: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 2: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 3: 1.) t-BuLi, 2.) CH3OH / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, - 85 deg C View Scheme

methanol; tert.-butyl lithium 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) -85 deg C;; Yield given. Multistep reaction;

1: 76 percent / aq. KOH / methanol; tetrahydrofuran / exothermic reaction 2: NaBH4 / ethanol; tetrahydrofuran / 1 h 3: aq. 48percent HBr / acetic acid / 0.5 h / 85 °C 4: 59 percent / H2 / W-2 Raney Nickel / ethanol; tetrahydrofuran / 6 h 5: 1.) t-butyllithium, 2.) methanol / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) -85 deg C; View Scheme

1: NaBH4 / ethanol; tetrahydrofuran / 1 h 2: aq. 48percent HBr / acetic acid / 0.5 h / 85 °C 3: 59 percent / H2 / W-2 Raney Nickel / ethanol; tetrahydrofuran / 6 h 4: 1.) t-butyllithium, 2.) methanol / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) -85 deg C; View Scheme

1: aq. 48percent HBr / acetic acid / 0.5 h / 85 °C 2: 59 percent / H2 / W-2 Raney Nickel / ethanol; tetrahydrofuran / 6 h 3: 1.) t-butyllithium, 2.) methanol / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) -85 deg C; View Scheme

1: 76 percent / aq. KOH / methanol; tetrahydrofuran / exothermic reaction 2: NaBH4 / ethanol; tetrahydrofuran / 1 h 3: aq. 48percent HBr / acetic acid / 0.5 h / 85 °C 4: 59 percent / H2 / W-2 Raney Nickel / ethanol; tetrahydrofuran / 6 h 5: 1.) t-butyllithium, 2.) methanol / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) -85 deg C; View Scheme