1H-imidazole in N,N-dimethyl-formamide

1: 73 percent / potassium permanganate / H2O; ethanol / 1.) -10 deg C, 1 h, 2.) to 40 deg C, 10 min 2: 86 percent / imidazole / dimethylformamide / 2 h / Ambient temperature 3: 1.) lead tetraacetate, 2.) Red-Al / 1.) benzene, pyridine, 25 deg C, 10 min, 2.) water, 1,5h 4: 91 percent / N-chlorosuccinimide, dimethyl sulfide / 1.) CH2Cl2, -20 deg C, 30 min, 2.) 0 deg C, 30 min 5: 1.) n-butyllithium, 2.) 5percent H2O2 / 1.) hexane, THF,-50 deg C, 15 min, 2.) chloroform, 1 min View Scheme

1: 86 percent / imidazole / dimethylformamide / 2 h / Ambient temperature 2: 1.) lead tetraacetate, 2.) Red-Al / 1.) benzene, pyridine, 25 deg C, 10 min, 2.) water, 1,5h 3: 91 percent / N-chlorosuccinimide, dimethyl sulfide / 1.) CH2Cl2, -20 deg C, 30 min, 2.) 0 deg C, 30 min 4: 1.) n-butyllithium, 2.) 5percent H2O2 / 1.) hexane, THF,-50 deg C, 15 min, 2.) chloroform, 1 min View Scheme

1: 91 percent / N-chlorosuccinimide, dimethyl sulfide / 1.) CH2Cl2, -20 deg C, 30 min, 2.) 0 deg C, 30 min 2: 1.) n-butyllithium, 2.) 5percent H2O2 / 1.) hexane, THF,-50 deg C, 15 min, 2.) chloroform, 1 min View Scheme

1: 1.) lead tetraacetate, 2.) Red-Al / 1.) benzene, pyridine, 25 deg C, 10 min, 2.) water, 1,5h 2: 91 percent / N-chlorosuccinimide, dimethyl sulfide / 1.) CH2Cl2, -20 deg C, 30 min, 2.) 0 deg C, 30 min 3: 1.) n-butyllithium, 2.) 5percent H2O2 / 1.) hexane, THF,-50 deg C, 15 min, 2.) chloroform, 1 min View Scheme

n-butyllithium; dihydrogen peroxide 1.) hexane, THF,-50 deg C, 15 min, 2.) chloroform, 1 min; Yield given. Multistep reaction;

1: 89 percent / n-butyllithium / -78 °C 2: 2. tetra-n-butylammonium fluoride / 1. diethyl ether, -78 deg C, 2. THF View Scheme

n-butyllithium T=-78°C;

1: 95 percent / n-BulI / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -92 deg C 2: 50 percent / CuI, Zn / ethanol; H2O / 1.33 h / ultrasonically induced reaction View Scheme

1: 89 percent / n-butyllithium / -78 °C 2: 2. tetra-n-butylammonium fluoride / 1. diethyl ether, -78 deg C, 2. THF View Scheme