5 Pd(II)/C(eggshell); hydrogen; trifluoroacetic acid in dichloromethane T=0°C; reductive Friedel-Crafts alkylation; P=760.051 Torr;

5 Pd(II)/C(eggshell); hydrogen in tetrahydrofuran T=20°C; P=760.051 Torr; 12 h;

diborane in tetrahydrofuran T=0 - 25°C; other solvent, other reagent;

1: 1.) ethyl magnesium bromide, 2.) 10percent aqueous ammonium chloride / 1.) Et2O, reflux, 2h, 2.) 30 min 2: 91 percent / B2H6 / tetrahydrofuran / 0 - 25 °C / other solvent, other reagent View Scheme