1: 81 percent / H2SO4 2: 95 percent / K2CO3 / acetone / 5 h / 50 °C 3: 92 percent / LiAlH4 View Scheme

1: 74 percent / 1 M NaHCO3 / 0.5 h / Ambient temperature 2: 66 percent / DCCD / dioxane / 5 h / Ambient temperature 3: 36 percent / NaHCO3 / H2O; dioxane / 24 h View Scheme

1: aq. NaOH solution / anschliessendes Erwaermen mit wss. Natronlauge 2: thionyl chloride 3: xylene; palladium/barium sulfate / 150 °C / Hydrogenation 4: ethanol; aqueous methanol. KOH / unter Kuehlung 5: acetic acid; ethanol; aqueous hydrochloric acid / Reduktion an Blei-Kathoden View Scheme

2.1: 32 percent / K2CO3 / dimethylformamide / 72 h / 80 °C 3.1: 100 percent / K2CO3 / dimethylformamide / 3 h / 0 °C 4.1: 97 percent / DIBAH / CH2Cl2 / 3 h / -78 °C 5.1: 76 percent / PCC / CH2Cl2 / 2 h / 20 °C 6.1: 30 percent aq. hydrogen peroxide; phenylselenic acid / CH2Cl2 / 48 h / 20 °C 6.2: KOH / methanol / 0.5 h / 20 °C 7.1: KOH / dimethylsulfoxide / 3 h / 20 °C 8.1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / methanol / 18 h / 20 °C 9.1: 98 percent / pyridine / diethyl ether / 4 h / 20 °C 10.1: AlCl3 / CH2Cl2 / 3 h / 20 °C 10.2: 94 percent / aq. HCl / methanol / 0.5 h / Heating 11.1: 60 percent / Huenig base / CH2Cl2 / 24 h / 20 °C 12.1: 77 percent / aq. K2CO3; n-Bu3NHSO4 / benzene / 20 h / 20 °C 13.1: NaH / dimethylsulfoxide / 3 h / 20 °C 13.2: aq. oxalic acid / 0 °C 13.3: AcOH; conc. HCl / 1.5 h 14.1: (COCl)2; DIPEA; DMSO / CH2Cl2 / 0.5 h / -78 - 20 °C 15.1: HMPA / tetrahydrofuran / 16 h / -85 - 20 °C View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 12.5 h / 40 °C / |Inert atmosphere 1.3: 12 h / |Reflux 2.1: HATU / dichloromethane / 20 °C / pH 5 3.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran; methanol / 13 °C View Scheme

1.1: H2SO4 2.1: Na2B4O7; H2SO4 3.1: K2CO3 / acetone 4.1: 77 percent / HNO3 / 2 h / 0 - 5 °C 5.1: 34 percent / SnCl2*2H2O; aq. HCl / 0.5 h / Heating 6.1: NaNO2; aq. HBr / 0 - 5 °C 6.2: 69 percent / CuBr; aq. HBr 7.1: 81 percent / aq. KOH / 5 h / Heating View Scheme

sodium hydroxide; water

sodium hydroxide; water

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