1: 0.884 g / dimethylformamide / 20 deg C, 3 h; 60 - 65 deg C, 5 h 2: 95 percent / KOH, H2O / ethanol / 2.5 h / Heating View Scheme

1: dimethylformamide / 48 h / Ambient temperature 2: KOH / aq. ethanol / 48 h / Heating 3: diethyl ether 4: N-bromosuccinimide / 1,2-dimethoxy-ethane; H2O / Ambient temperature 5: MeONa / methanol / 0.5 h / Ambient temperature 6: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 7: LiAlH4 / diethyl ether / 2 h 8: H2 / Adams' platinum oxide / methanol 9: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 10: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 11: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: 80 percent 2: 84.5 percent / n-BuLi / hexane; tetrahydrofuran / 1.5 h / -70 °C 3: 83 percent / Li, NH3 / diethyl ether / 4 h / -25 °C 4: 86 percent / H2SO4 (conc.) / acetone; H2O / 4 h / Heating View Scheme