sodium cyanide in dimethyl sulfoxide T=180 - 185°C; 2 h;

1: 1.) NaH / 1.) DMF, 0 -5 deg C, 20 min, 2.) DMF, RT, 20 h 2: NaCN / dimethylsulfoxide / 2 h / 180 - 185 °C View Scheme

1: 5percent HCl 2: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h 3: 82 percent / diphenyl ether / 4 h / 190 - 205 °C 4: 56 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature 5: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature 6: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 7: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 8: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme