N,N,N',N',N'',N''-hexamethylphosphoric triamide; thionyl chloride in tetrahydrofuran T=20°C;

1: POCl3 / 1,2-dichloro-ethane / 17 h / Heating 2: 76 percent / NaOH; Ag2O / H2O / 20 - 50 °C 3: 83 percent / H2SO4 / toluene / 7 h / Heating 4: LiAlH4 / diethyl ether / Heating 5: HMPA; thionyl chloride / tetrahydrofuran / 20 °C View Scheme

1.1: AlCl3 / CS2 / 2.5 h / 20 °C 2.1: dimethylformamide / 22 h / 5 °C 3.1: H2SO4 / methanol / 1 h / Heating 3.2: chloranil / benzene / 2 h / Heating 4.1: POCl3 / 1,2-dichloro-ethane / 17 h / Heating 5.1: 76 percent / NaOH; Ag2O / H2O / 20 - 50 °C 6.1: 83 percent / H2SO4 / toluene / 7 h / Heating 7.1: LiAlH4 / diethyl ether / Heating 8.1: HMPA; thionyl chloride / tetrahydrofuran / 20 °C View Scheme

1: 83 percent / H2SO4 / toluene / 7 h / Heating 2: LiAlH4 / diethyl ether / Heating 3: HMPA; thionyl chloride / tetrahydrofuran / 20 °C View Scheme

1: 76 percent / NaOH; Ag2O / H2O / 20 - 50 °C 2: 83 percent / H2SO4 / toluene / 7 h / Heating 3: LiAlH4 / diethyl ether / Heating 4: HMPA; thionyl chloride / tetrahydrofuran / 20 °C View Scheme

1.1: dimethylformamide / 22 h / 5 °C 2.1: H2SO4 / methanol / 1 h / Heating 2.2: chloranil / benzene / 2 h / Heating 3.1: POCl3 / 1,2-dichloro-ethane / 17 h / Heating 4.1: 76 percent / NaOH; Ag2O / H2O / 20 - 50 °C 5.1: 83 percent / H2SO4 / toluene / 7 h / Heating 6.1: LiAlH4 / diethyl ether / Heating 7.1: HMPA; thionyl chloride / tetrahydrofuran / 20 °C View Scheme

1: LiAlH4 / diethyl ether / Heating 2: HMPA; thionyl chloride / tetrahydrofuran / 20 °C View Scheme

1.1: H2SO4 / methanol / 1 h / Heating 1.2: chloranil / benzene / 2 h / Heating 2.1: POCl3 / 1,2-dichloro-ethane / 17 h / Heating 3.1: 76 percent / NaOH; Ag2O / H2O / 20 - 50 °C 4.1: 83 percent / H2SO4 / toluene / 7 h / Heating 5.1: LiAlH4 / diethyl ether / Heating 6.1: HMPA; thionyl chloride / tetrahydrofuran / 20 °C View Scheme

1: 18-crown-6 / acetonitrile / 20 °C 2: KOH / ethanol; H2O / Heating View Scheme

18-crown-6 ether in acetonitrile T=20°C;