1: 84 percent / BuLi / tetrahydrofuran / 0.42 h / -20 °C 2: 100 percent / H2, Et3N / Pd/C / ethyl acetate / 3 h / Ambient temperature 3: 100 percent / H2, Pd(OH)2 / ethanol / 5 h 4: 98 percent / 1.) (COCl)2; 2.) Et3N / dimethylsulfoxide / 1.) -78 deg C, 30 min; 2.) RT, 30 min View Scheme

diisobutylaluminium hydride in diethyl ether; n-heptane T=-78°C; 0.5 h;

diisobutylaluminium hydride in diethyl ether; toluene T=-78°C; Reduction; 6 h;

1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-72°C; 1.25 h; 2: With triethylamine in dichloromethane T=-72 - 20°C;

diisobutylaluminium hydride in tetrahydrofuran; hexane T=-78°C; 0.6 h; Inert atmosphere;

1: imidazole 2: DIBAL-H / -78 °C View Scheme

Yield given. Multistep reaction;