sodium hydroxide; iodine in methanol; diethyl ether T=20°C; Grignard reaction; rearrangement; 0.25 h;

1: 1.) lithium amide / 1.) liquid ammonia, 3 h; 2.) THF, 3 h 2: 90 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 80 percent / PBr3 / pyridine; diethyl ether / 2 h / Heating 4: 1.) Mg, 1,2-dibromoethane; 2.) Li2CuCl4 / 1.) THF; 2.) THF, -10 deg C, 4 h View Scheme

1: 1.) lithium amide / 1.) liquid ammonia, 3 h; 2.) THF, 3 h 2: 90 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 80 percent / PBr3 / pyridine; diethyl ether / 2 h / Heating 4: 1.) Mg, 1,2-dibromoethane; 2.) Li2CuCl4 / 1.) THF; 2.) THF, -10 deg C, 4 h View Scheme

1: 90 percent / H2, quinoline / Lindlar's catalyst / hexane 2: 80 percent / PBr3 / pyridine; diethyl ether / 2 h / Heating 3: 1.) Mg, 1,2-dibromoethane; 2.) Li2CuCl4 / 1.) THF; 2.) THF, -10 deg C, 4 h View Scheme

1: CH2Cl2 / 4 h / 25 °C 2: diethyl ether / 2 h / 25 °C 3: 84 percent / I2; NaOH / diethyl ether; methanol / 0.25 h / 20 °C View Scheme

1: 80 percent / PBr3 / pyridine; diethyl ether / 2 h / Heating 2: 1.) Mg, 1,2-dibromoethane; 2.) Li2CuCl4 / 1.) THF; 2.) THF, -10 deg C, 4 h View Scheme

dilithium tetrachlorocuprate; magnesium; ethylene dibromide 1.) THF; 2.) THF, -10 deg C, 4 h; Yield given. Multistep reaction;

Yield given. Multistep reaction;