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in pyridine 1 h; Heating;

1: 71 percent / DMSO, NaY / tetrahydrofuran / 0.5 h 2: pyridine View Scheme

1: 90 percent / acetonitrile 2: 71 percent / DMSO, NaY / tetrahydrofuran / 0.5 h 3: pyridine View Scheme

1: 71 percent / DMSO, NaY / tetrahydrofuran / 0.5 h 2: pyridine View Scheme

tetramethylstannane; tungsten hexachloride T=70°C; 5 h;

1: 75 percent / 20 h / 155 °C 2: 1.) BuLi / 1.) THF, hexane, 2 h, -20 deg C, 2.) 30 min, -78 degC 3: LiAlH4 / diethyl ether / 1 h / 0 °C 4: p-toluenesulfonic acid / methanol; H2O / 3 h / Heating 5: 87 percent / pyridine / 1 h / Heating View Scheme

1: 63 percent / PBr3 / petroleum ether / 1.) 1 h, 0 deg C, 2.) 3 h, room temp. 2: 75 percent / 20 h / 155 °C 3: 1.) BuLi / 1.) THF, hexane, 2 h, -20 deg C, 2.) 30 min, -78 degC 4: LiAlH4 / diethyl ether / 1 h / 0 °C 5: p-toluenesulfonic acid / methanol; H2O / 3 h / Heating 6: 87 percent / pyridine / 1 h / Heating View Scheme

1: 41 percent / LiAlH4 / diethyl ether 2: 63 percent / PBr3 / petroleum ether / 1.) 1 h, 0 deg C, 2.) 3 h, room temp. 3: 75 percent / 20 h / 155 °C 4: 1.) BuLi / 1.) THF, hexane, 2 h, -20 deg C, 2.) 30 min, -78 degC 5: LiAlH4 / diethyl ether / 1 h / 0 °C 6: p-toluenesulfonic acid / methanol; H2O / 3 h / Heating 7: 87 percent / pyridine / 1 h / Heating View Scheme

1: 83 percent / benzene / 48 h / Heating 2: 41 percent / LiAlH4 / diethyl ether 3: 63 percent / PBr3 / petroleum ether / 1.) 1 h, 0 deg C, 2.) 3 h, room temp. 4: 75 percent / 20 h / 155 °C 5: 1.) BuLi / 1.) THF, hexane, 2 h, -20 deg C, 2.) 30 min, -78 degC 6: LiAlH4 / diethyl ether / 1 h / 0 °C 7: p-toluenesulfonic acid / methanol; H2O / 3 h / Heating 8: 87 percent / pyridine / 1 h / Heating View Scheme