aluminium trichloride in dichloromethane T=20°C; Friedel-Crafts condensation; 4 h;

titanium tetrachloride in dichloromethane 1 h; Ambient temperature;

PPA T=100°C; 0.166667 h;

1: 1) H2; 2) NaH / 1) 10percent Pt-C / 1) THF, 5 h, 59 -> 27 lb/square inch; 2) THF, reflux, 5 h 2: 81 percent / KOH / ethanol / 14 h / Heating 3: 84 percent / Ac2O / 2 h / Heating 4: 90 percent / TiCl4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 93 percent / piperidine, HOAc / benzene / 14 h / Heating 2: 1) H2; 2) NaH / 1) 10percent Pt-C / 1) THF, 5 h, 59 -> 27 lb/square inch; 2) THF, reflux, 5 h 3: 81 percent / KOH / ethanol / 14 h / Heating 4: 84 percent / Ac2O / 2 h / Heating 5: 90 percent / TiCl4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 84 percent / Ac2O / 2 h / Heating 2: 90 percent / TiCl4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 81 percent / KOH / ethanol / 14 h / Heating 2: 84 percent / Ac2O / 2 h / Heating 3: 90 percent / TiCl4 / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 88 percent / triethylsilane; CF3COOH / 0.5 h / 0 °C 2: 81 percent / tetrahydrofuran / 2 h / 0 °C 3: 85 percent / O2; t-BuOK; P(OEt)3 / dimethylformamide / 1 h / -15 - -10 °C 4: 87 percent / AlCl3 / nitrobenzene / 0 °C View Scheme

pyridine; sodium tetrahydroborate; acetic anhydride 1a) 2 h, -15 deg C, 1b) 1 h, 0 deg C, 1c) 2 h, room temp., 2) 100 deg C, 2 h; Yield given. Multistep reaction;

1: 85 percent / HCl / 1.5 h / Heating 2: 63 percent / BCl3 / CH2Cl2 / 0.17 h / Ambient temperature 3: 81 percent / conc.HCl, H2 / platinum oxide / methanol 4: 82.5 percent / K2CO3 / dimethylformamide / 4 h / 80 °C 5: 92 percent / NaOH / H2O; methanol / 3 h / Heating 6: 77.5 percent / diethyl ether / 4 h / Ambient temperature 7: 91.5 percent / H2 / Pd-C / ethyl acetate View Scheme