triethylamine; trichlorophosphate in dichloromethane

1: (EtO)2P(O)CH2NC With sodium hexamethyldisilazane in tetrahydrofuran T=-78°C; Metallation; 0.25 h; 2: 1H-indole-3-carbaldehyde in tetrahydrofuran T=0°C; Horner-Emmons reaction; 20 h;

Yield given. Multistep reaction;

1: potassium tert-butylate / CH2Cl2 / 1 h / -70 °C 2: 37percent HCl / diethyl ether / 0.17 h / Ambient temperature 3: trifluoroacetic acid / 0.5 h / Ambient temperature View Scheme

1: potassium tert-butylate / CH2Cl2 / 0.25 h / -70 °C 2: potassium tert-butylate / 1) methylene dichloride, -70 deg C, 1h; 2) room temperature, ethanol, glacial acetic acid 3: 85 percent / 37percent HCl / ethanol / 20 h / Ambient temperature View Scheme

copper(I) oxide in benzene 15 h; Heating;