1: 87 percent / DIPEA / CH2Cl2 / 5 h / 0 - 20 °C 2: 98 percent / LiAlH4 / diethyl ether / 2 h / 0 - 20 °C 3: 93 percent / N-bromosuccinimide / dimethylformamide / 2 h / 0 °C 4: 95 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C 5: 95 percent / n-BuLi / hexane; diethyl ether / 3 h / -78 - 20 °C 6: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 7: 72 percent / K2CO3 / acetone / 1 h / 20 °C 8: 90 percent / Cs2CO3 / dimethylformamide / 1 h / 20 °C 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 3.25 h / -78 - 20 °C 10: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C 11: 79 percent / H2 / Pd/C / ethanol / 1 h / 20 °C / 760 Torr 12: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 13: aq. NaH2PO4; NaClO2; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 20 °C 14: 203 mg / diethyl ether; methanol / 0.17 h / 20 °C 15: 81 percent / p-TsOH / methanol / 4 h / Heating View Scheme

1: K2CO3 / acetone / 20 h / Heating 2: 90 percent / 10percent aq. NaOH / acetone / 2 h / Heating 3: 65 percent / SOCl2 / benzene / 5 h / Heating View Scheme

1: 32 percent / potassium carbonate / acetone / 18 h / Heating 2: 89 percent / 1.) lithium aluminium hydride / diethyl ether / 1.) reflux, 3 h, 2.) 16 h 3: phosphorus tribromide / tetrahydrofuran; benzene / 1.) 0 deg C, 2.) 20 deg C, 3.5 h 4: 61 percent / benzene / 6 h / Heating 5: 73 percent / 1.) n-butyl-lithium / tetrahydrofuran; hexane / 1.) 20 deg C, 90 min, 2.) 20 deg C, 18 h 6: 71 percent / pyridine / 22 h 7: 97 percent / H2 / 10percent palladium on carbon / ethyl acetate / 16 h / 20 °C 8: 24 percent / potassium carbonate, potassium iodide, 18-crown-6 / acetone / 22 h / Heating 9: H2 / Lindlar catalyst / ethyl acetate / 0.33 h / 20 °C 10: 40 mg / 1.25 h / 150 °C 11: 90 percent / aqueous 10percent sodium hydroxide, ethanol / 1 h / 85 °C View Scheme

1: 79 percent / K2CO3 / acetone / 48 h / Heating 2: 97.5 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 81 percent / MnO2 / acetone / 1 h / 23 °C 4: 1.) potassium 2-methyl-2-butanolate / 1.) hexamethylphosphoric triamide, 0 deg C, 15 min, 2.) benzene, 20 deg C, 1 h 5: 87 percent / H2 / 10percent Pd/C / ethyl acetate View Scheme

1.1: 96 percent / K2CO3 / acetone / 12 h / Heating 2.1: 97 percent / LiAlH4 3.1: 84 percent / Et3N / CH2Cl2 / 0.33 h / 4 °C 4.1: 69 percent / benzyltriethylammonium chloride / H2O; CHCl3 / 2 h / Heating 5.1: 92 percent / aq. Ba(OH)2 / dioxane / 15 h / 115 °C 6.1: 99 percent / AcOH; 60 percent aq. HClO4 / 0.08 h / 35 °C 7.1: 97 percent / H2 / 5 percent Pd/C / ethanol 8.1: MeONa / methanol / 0.33 h / 60 °C 8.2: 20 percent / NaBH4 / methanol / 4 h / 60 °C 9.1: 76 percent / 1N NaOH / 3 h / 45 °C View Scheme

1: 96 percent / K2CO3; Adogen 464 / acetone / Heating 2: 86 percent / NaOH / methanol / Heating 3: SOCl2 / 2 h / Heating View Scheme

1: 100 percent / K2CO3 / acetonitrile / 100 °C 2: 92 percent / KOH / ethanol / 4 h / Heating 3: 99 percent / SOCl2 / Heating 4: 78 percent / Na2CO3 / acetone / 4 h / Heating 5: 81 percent / aq. NaOH / tetrahydrofuran / Heating View Scheme

caesium carbonate in N,N-dimethyl-formamide T=180°C; 3 h;

potassium carbonate in N,N-dimethyl-formamide T=120°C; Product distribution / selectivity;

sodium hydride in N,N-dimethyl-formamide T=20°C; 12 h;