sodium tetrahydroborate in tetrahydrofuran; ethanol T=20°C; 4 h;

trimethylaluminum in dichloromethane; toluene T=0 - 60°C;

1: SOCl2 / CH2Cl2 / Heating 2: NaBH4 View Scheme

1.1: triethylamine / 1,4-dioxane / 0.17 h / 0 °C 2.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0.83 h / 0 °C 4.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.17 h / -70 °C / Inert atmosphere 4.2: -78 °C / Inert atmosphere 5.1: 2,4,6-trimethyl-pyridine; oxalyl dichloride / dichloromethane / -50 °C / Inert atmosphere 6.1: sodium tetrahydroborate View Scheme

1: SOCl2 / 1 h / Heating 2: 147 g / benzene; tetrahydrofuran / 0 - 20 °C 3: 40 percent / Zn; AcOH / 6 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.17 h / -70 °C / Inert atmosphere 1.2: -78 °C / Inert atmosphere 2.1: 2,4,6-trimethyl-pyridine; oxalyl dichloride / dichloromethane / -50 °C / Inert atmosphere 3.1: sodium tetrahydroborate View Scheme

1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.17 h / -70 °C / Inert atmosphere 1.2: 5.5 h / -70 - 20 °C / Inert atmosphere 2.1: 2,4,6-trimethyl-pyridine; oxalyl dichloride / dichloromethane / -50 °C / Inert atmosphere 3.1: sodium tetrahydroborate View Scheme

1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0.83 h / 0 °C 3.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.17 h / -70 °C / Inert atmosphere 3.2: -78 °C / Inert atmosphere 4.1: 2,4,6-trimethyl-pyridine; oxalyl dichloride / dichloromethane / -50 °C / Inert atmosphere 5.1: sodium tetrahydroborate View Scheme

1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0.83 h / 0 °C 3.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.17 h / -70 °C / Inert atmosphere 3.2: 5.5 h / -70 - 20 °C / Inert atmosphere 4.1: 2,4,6-trimethyl-pyridine; oxalyl dichloride / dichloromethane / -50 °C / Inert atmosphere 5.1: sodium tetrahydroborate View Scheme

1: 147 g / benzene; tetrahydrofuran / 0 - 20 °C 2: 40 percent / Zn; AcOH / 6 h / Heating View Scheme