hydrogenchloride; sodium methylate in methanol

sodium methylate in methanol

palladium in quinoline; Petroleum ether

in tetrahydrofuran

in tetrahydrofuran T=-78°C; Addition;

magnesium 1.) THF, 2.) THF, RT, 1 h; Yield given. Multistep reaction;

1.1: CuCl2; NaCl; conc. aq. HCl / benzene / 5 h / 50 °C 2.1: 94 percent / NaBH4 / tetrahydrofuran / 0.5 h / -20 °C 3.1: POCl3 4.1: dimethylformamide / 20 °C 5.1: TsOH / methanol / 12 h / 20 °C 6.1: 65 percent / n-BuLi 7.1: 100 percent / LiBHEt3; Pd(dppp)Cl2 / tetrahydrofuran / 3 h / 0 °C 8.1: N-chlorosuccinimide; Me2S / CH2Cl2 / 2.5 h / 0 °C 9.1: n-BuLi 9.2: -78 - 20 °C 10.1: LiBHEt3; Pd(dppp)Cl2 / tetrahydrofuran 11.1: TBAF / tetrahydrofuran / 1 h 12.1: Cp2ZrCl2 / 1,2-dichloro-ethane; hexane 12.2: 83 percent / NiCl2(PPh3)2; n-BuLi / tetrahydrofuran; hexane View Scheme

1: 43 percent / aq. HCl, NaCl, CuC / toluene / 6 h / 50 °C 2: 54 percent / p-toluenesulfonic acid / cyclohexane / Heating 3: 1.) NaOCH3 / 1.) CH3OH, RT, 0.5 h, 2.) CH3OH, RT, overnight 4: aq. NaOH / 2 h / 60 °C 5: 1.) Mg / 1.) THF, 2.) THF, 30 deg C, 0.5 h 6: 79 percent / aq. oxalic acid / acetone / 1 h / Ambient temperature 7: KHSO4 / 180 °C View Scheme

1: 43 percent / aq. HCl, NaCl, CuC / toluene / 6 h / 50 °C 2: 54 percent / p-toluenesulfonic acid / cyclohexane / Heating 3: 1.) NaOCH3 / 1.) CH3OH, RT, 0.5 h, 2.) CH3OH, RT, overnight 4: aq. NaOH / 2 h / 60 °C 5: 1.) Mg / 1.) THF, 2.) THF, 30 deg C, 0.5 h 6: 79 percent / aq. oxalic acid / acetone / 1 h / Ambient temperature View Scheme

1.1: CuCl2; NaCl; conc. aq. HCl / benzene / 5 h / 50 °C 2.1: 94 percent / NaBH4 / tetrahydrofuran / 0.5 h / -20 °C 3.1: POCl3 4.1: dimethylformamide / 20 °C 5.1: TsOH / methanol / 12 h / 20 °C 6.1: 65 percent / n-BuLi 7.1: 100 percent / LiBHEt3; Pd(dppp)Cl2 / tetrahydrofuran / 3 h / 0 °C 8.1: N-chlorosuccinimide; Me2S / CH2Cl2 / 2.5 h / 0 °C 9.1: 79 percent / n-BuLi 10.1: LiBHEt3; Pd(dppp)Cl2 / tetrahydrofuran 11.1: TBAF / tetrahydrofuran 12.1: Cp2ZrCl2 / 1,2-dichloro-ethane; hexane 12.2: 89 percent / NiCl2(PPh3)2; n-BuLi / tetrahydrofuran; hexane View Scheme