pyridine; pivaloyl chloride in dichloromethane T=20°C;

1: zinc cyanide With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) 0.166667 h; 2: 4-(4-oxocyclohexyl)phenyl trifluoromethanesulfonate in N,N-dimethyl-formamide T=120°C; Product distribution / selectivity;

in tert-butyl methyl ether; water; ethyl acetate; acetone

hydrogen; palladium on activated charcoal in ethyl acetate 19 h; Product distribution / selectivity;

1.1: AlCl3, aluminium chloride / dichloromethane / 3 h / 0 - 20 °C 1.2: 0 °C / pH 10 2.1: pivaloyl chloride; pyridine / dichloromethane / 20 °C View Scheme

toluene-4-sulfonic acid 2 h; Reflux;

1: 94 percent / t-BuOK / various solvent(s); tetrahydrofuran / 2.75 h / -10 - 25 °C 2: 29 percent / 2N HCl / tetrahydrofuran / 0.5 h / Heating 3: 1.) t-BuOK; 2.) 2N HCl / 1.) t-butyl methyl ether, -10 deg C - RT, 165 min; 2.) THF, reflux, 30 min 4: 1.) t-BuOK; 2.) 2N HCl / 1.) t-butyl methyl ether, -10 deg C - RT, 165 min; 2.) THF, reflux, 30 min 5: 1.) t-BuOK; 2.) 2N HCl / 1.) t-butyl methyl ether, -10 deg C - RT, 165 min; 2.) THF, reflux, 30 min 6: 0.8 M n-BuLi / tetrahydrofuran; hexane / 1.17 h / -20 °C View Scheme

1: 94 percent / t-BuOK / various solvent(s); tetrahydrofuran / 2.75 h / -10 - 25 °C 2: 29 percent / 2N HCl / tetrahydrofuran / 0.5 h / Heating 3: t-BuOK / various solvent(s) / 1.) RT, 1 h, -60 deg C, 15 min, -30 deg C, 1 h View Scheme