trichlorophosphate T=0 - 20°C; 2.5 h;

1.1: 90 percent / phosphoryl chloride / 0 - 40 °C 2.1: NaOH / CH2Cl2 / 20 °C 2.2: 95 percent / CH2Cl2 / 20 °C View Scheme

1.1: 90 percent / phosphoryl chloride / 0 - 40 °C 2.1: NaOH / CH2Cl2 / 20 °C 2.2: 95 percent / CH2Cl2 / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 3.3: 65 percent / tetrahydrofuran; hexane / -78 - 0 °C 4.1: 91 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 90 percent / phosphoryl chloride / 0 - 40 °C 2.1: NaOH / CH2Cl2 / 20 °C 2.2: 95 percent / CH2Cl2 / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 3.3: 62 percent / tetrahydrofuran; hexane / -78 - 0 °C 4.1: 83 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 90 percent / phosphoryl chloride / 0 - 40 °C 2.1: NaOH / CH2Cl2 / 20 °C 2.2: 95 percent / CH2Cl2 / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 3.3: 84 percent / tetrahydrofuran; hexane / -78 - 0 °C 4.1: 91 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 90 percent / phosphoryl chloride / 0 - 40 °C 2.1: NaOH / CH2Cl2 / 20 °C 2.2: 95 percent / CH2Cl2 / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 3.3: 94 percent / tetrahydrofuran; hexane / -78 - 0 °C 4.1: 91 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1.1: 90 percent / phosphoryl chloride / 0 - 40 °C 2.1: NaOH / CH2Cl2 / 20 °C 2.2: 95 percent / CH2Cl2 / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C 3.3: 71 percent / tetrahydrofuran; hexane / -78 - 0 °C 4.1: 94 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme

1: 98 percent / AcOH / 17.5 h / 6 - 21 °C / Et2NH in AcOH and 30 min after aq. CH2O mixing at 6 deg C; pouring into a pre-cooled indole; quenching with 10 percent NaOH 2: 90 percent / tetrahydrofuran; H2O / MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar 3: 77 percent / Na / 2.5 h / 90 - 105 °C / Na adding insmall portions to a soln. of the indole in (EtO)2CO at 90 deg C; stirring 2 h at 105 deg C; evapg. 4: 91 percent / H2 / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac2O 5: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 6: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme

potassium hydroxide in ethanol Heating / reflux;

in acetic acid