1: 95 percent / LiAlH4 / diethyl ether 2: 93 percent / pyridinium chlorochromate, CH3COONa / CH2Cl2 / 1 h 3: 92 percent / diethyl ether / 2 h / Ambient temperature 4: p-toluenesulfonic acid / benzene / Heating 5: H2 / 10percent Pd/C / ethanol View Scheme

1: NaOH 2: 82 percent / LAH 3: 92 percent / PBr3 / pyridine 4: 80 percent / NaOMe / dimethylformamide 5: 80 percent / BBr3 View Scheme

1.1: aq. KOH / ethanol / 20 °C 2.1: SOCl2 3.1: Et3N / tetrahydrofuran / 0 °C 4.1: silver benzoate; Et3N / methanol 4.2: aq. KOH / methanol View Scheme

1: 76 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) r.t., 1 h 2: 3 percent / manganese(III) acetate, acetic acid / 22 h / Ambient temperature View Scheme

1: 1) 50percent NaH / 1) DMSO, 60 deg C, 90 min, 2) THF, 60 deg C, 1 h 2: 72 percent / Zn / methanol; acetic acid / 0.08 h 3: H2 / Pd/C / acetone View Scheme

1: NaOH / ethanol / 1.5 h / Heating 2: thionyl chloride / benzene / 1 h / Heating 3: Et3N / diethyl ether / 4 h 4: 86 percent / silver benzoate, Et3N / 1 h / Heating 5: 55 percent / AcOH, perchloric acid (3 drops) / 0.25 h / Ambient temperature 6: NaH / tetrahydrofuran / 2 h / Ambient temperature 7: tetrahydrofuran / 0.5 h 8: 27 percent / ethanol / 1 h / Irradiation 9: 9 percent / KOH (40percent) / ethanol; dioxane / 2.5 h / Heating 10: 65 percent / potassium dichromate / dioxane; acetic acid / 5 h / Ambient temperature 11: 28 percent / MnO2, H2SO4 (conc.) / 0.5 h / 60 °C 12: silver oxide / dioxane / 1.5 h / Ambient temperature View Scheme

1: 95 percent / LiAlH4 / diethyl ether 2: 93 percent / pyridinium chlorochromate, CH3COONa / CH2Cl2 / 1 h View Scheme

1: 88 percent / LiAlH4 / diethyl ether / 4 h / 20 °C 2: 42 percent / phosphorous tribromide / CH2Cl2 / 5 h / 0 - 20 °C View Scheme

lithium aluminium tetrahydride in diethyl ether

potassium carbonate in N,N-dimethyl-formamide T=20°C; 2 h;