sodium tetrahydroborate; ozone 1.) MeOH, 5 deg C, 2.) MeOH, < 20 deg C, 5 h; Yield given. Multistep reaction;

lithium aluminium tetrahydride; toluene-4-sulfonic acid 1.) C6H6; Multistep reaction;

1H-imidazole; iodine; triphenylphosphine in benzene 0.666667 h; Ambient temperature;

1: pyridinium chlorochromate (PCC), NaOAc / CH2Cl2 / 3 h / Ambient temperature 2: n-BuLi in hexane / 1) THF, 0.5 h, room temperature, 2) 3 h, room temperature View Scheme

1: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.75 h / 25 °C 2: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 3: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 4: 93 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C 5: 86 percent / hydrochloric acid / diethyl ether / 3 h / 25 °C 6: 97 percent / pyridine 7: 1.) sodium iodide, 2.) DBU / 1.) DMF, 50 deg C, 3.5 h, 2.) 80 deg C, 3.5 h 8: 1.) sodium hydride, 3.) aluminum chloride, lithium aluminum hydride / 1.) ether, 25 deg C, 1 h, 2.) 10 h, 3.) 0 deg C, 1 h View Scheme

1: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.75 h / 25 °C 2: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 3: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 4: 93 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C 5: 86 percent / hydrochloric acid / diethyl ether / 3 h / 25 °C 6: 97 percent / pyridine 7: 1.) sodium iodide, 2.) DBU / 1.) DMF, 50 deg C, 3.5 h, 2.) 80 deg C, 3.5 h View Scheme

sodium acetate; pyridinium chlorochromate in dichloromethane T=25°C; 0.75 h;

1: 78 percent / LiBr, TMSCl / acetonitrile / 15 h / Heating 2: 96 percent / p-TsOH / benzene / 5 h / Heating View Scheme

1: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.75 h / 25 °C 2: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 3: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 4: 86 percent / hydrochloric acid / diethyl ether / 1 h / 25 °C View Scheme

1: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.75 h / 25 °C 2: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h 3: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C 4: 93 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C 5: 86 percent / hydrochloric acid / diethyl ether / 3 h / 25 °C 6: 97 percent / pyridine 7: 1.) sodium iodide, 2.) DBU / 1.) DMF, 50 deg C, 3.5 h, 2.) 80 deg C, 3.5 h 8: 1.) sodium hydride, 3.) aluminum chloride, lithium aluminum hydride / 1.) ether, 25 deg C, 1 h, 2.) 10 h, 3.) 0 deg C, 1 h View Scheme