1: Chirald, LiAlH4 / diethyl ether / 1.) -100 deg C, 2 h, 2.) -70 to -65 deg C, 2 h 2: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme

Yield given. Multistep reaction. Title compound not separated from byproducts;

copper(I) bromide dimethylsulfide complex

aluminium trichloride in dichloromethane 1.) -65 deg C, 2.5 h, then -40 deg C, 1 h, 2.) -30 deg C, 2 h, then -30 deg C to 0 deg C, 15 h;

in tetrahydrofuran -65 deg C, 3 h -> room temperature, 20 h;

1: 86.2 percent / n-butyllithium / tetrahydrofuran / 15 h / 1.) 3 deg C, 1 h, 2.) -50 deg C to r.t., 15 h 2: 70.1 percent / AlCl3 / CH2Cl2 / 1.) -65 deg C, 2.5 h, then -40 deg C, 1 h, 2.) -30 deg C, 2 h, then -30 deg C to 0 deg C, 15 h View Scheme