ammonium hydroxide T=20°C; 17 h;

sodium tetrahydroborate; di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran T=25 - 75°C; 21 h; Inert atmosphere; regioselective reaction;

1: aqueous NaOH 2: diethyl ether View Scheme

diethyl ether

pyridinium tribromide; triethylamine in dichloromethane T=0°C; 2 h;

in chloroform

1: 80 percent / pyridinium hydrobromide perbromide, triethylamine / CHCl3 / 0 °C 2: 1.) NaH / 1.) THF, 0 deg C, 45 min, 2.) THF, RT, 2 h 3: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, from -78 deg C to RT 4: 1.) boron trifluoride etherate, 2.) Triton B / 1.) CH2Cl2, RT, 2 h, 2.) acetonitrile, methanol View Scheme

aluminium trichloride 1.) CH2Cl2, room temperature, 15 min, 2.) room temperature, 10 min; Yield given. Multistep reaction;