toluene-4-sulfonic acid in benzene 24 h; Heating;

1: 83 percent / t-BuOK / diethyl ether; 2-methyl-propan-2-ol / 5 h / Heating 2: 98 percent / toluene-p-sulphonic acid / benzene / 24 h / Heating View Scheme

1: methylmagnesium chloride / solvent:THF 2: 95 percent / pyridine / 18 h / -10 °C 3: 79 percent / DIBAL-H / toluene / 5 h / -50 °C 4: 85 percent / triethylamine / dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C 5: 72 percent / Sodium iodide, triethylamine / dimethylsulfoxide / 12 h / Ambient temperature 6: 65 percent / triethylamine, Pd(PPh3)4 / acetonitrile / 1.) - 78 deg C, 2.) 150 deg C, 24 h; sealed tube View Scheme

magnesium 1.) THF, 2.) THF; Yield given. Multistep reaction;

1: 1.) Mg, 1,2-dibromoethane / 1.) THF, -78 deg C, 30 min, 2.) room temperature, 15 h 2: 7.9 g / pyridinium toluene-p-sulphonate / ethanol / 5 h / 60 °C View Scheme

1: methylmagnesium chloride / solvent:THF 2: 95 percent / pyridine / 18 h / -10 °C View Scheme

magnesium; ethylene dibromide 1.) THF, -78 deg C, 30 min, 2.) room temperature, 15 h; Yield given. Multistep reaction;

Yield given. Multistep reaction;

1.) Li, ether, 2-4 deg C, 30 min 2.) 0 deg C, 30 min; Yield given. Multistep reaction;