sodium iodide in acetone 0.0833333 h;

sodium iodide in acetone 24 h;

1: 92 percent / dimethylsulfoxide / 20 h / 80 °C 2: 85 percent / 10percent aq. NaOH / methanol / Heating 3: 82 percent / p-toluenesulfonic acid / methanol / 20 h 4: 53 percent / I2, (4-dimethylaminophenyl)diphenylphosphine / diethyl ether / 0.25 h / 0 °C View Scheme

1: 85 percent / dimethylformamide / 3 h / 120 °C 2: 92 percent / K2CO3 / methanol / 18 h 3: 82 percent / pyridinium dichromate / dimethylformamide 4: 82 percent / p-toluenesulfonic acid / methanol / 20 h 5: 53 percent / I2, (4-dimethylaminophenyl)diphenylphosphine / diethyl ether / 0.25 h / 0 °C View Scheme

1: 82 percent / pyridinium dichromate / dimethylformamide 2: 82 percent / p-toluenesulfonic acid / methanol / 20 h 3: 53 percent / I2, (4-dimethylaminophenyl)diphenylphosphine / diethyl ether / 0.25 h / 0 °C View Scheme

1: 86 percent / p-toluenesulfonic acid / methanol / 20 h 2: 53 percent / I2, (4-dimethylaminophenyl)diphenylphosphine / diethyl ether / 0.25 h / 0 °C View Scheme

Multistep reaction;

(i) aq. HCl, MeOH, (ii) CrO3, acetone, (iii) /BRN= 102415/, Et2O; Multistep reaction;

1: 1.) t-C4H9Li; copper(I) iodide, tributylphosphine; 3.) triphenyltin chloride / 1.) ether-pentane, -95 deg C, -78 deg C 3h; THF -78 deg C 15 min; 2.) ether, pentane, THF, -78 deg C 3.5 h, HPMA, -78 deg C 30 min; 3.) ether, pentane, THF, HMPA, -30 deg C, 39 h 2: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 3: 98 percent / 15percent hydrogen fluoride/pyridine mixture / acetonitrile / 1.) 0 deg C; 2.) 24 deg C, 30 min; 3.) 24 deg C, 3 h View Scheme

1: 1.) t-C4H9Li; copper(I) iodide, tributylphosphine; 3.) triphenyltin chloride / 1.) ether-pentane, -95 deg C, -78 deg C 3h; THF -78 deg C 15 min; 2.) ether, pentane, THF, -78 deg C 3.5 h, HPMA, -78 deg C 30 min; 3.) ether, pentane, THF, HMPA, -30 deg C, 39 h 2: 87 percent / hydrogen, synthetic quinoline / palladium on barium sulfate / benzene; cyclohexane / 1.) 25 deg C, 3 h; 2.) 40 deg C, 4.5 h 3: 1.) L-Selectride; 2.) 3percent H2O2 / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C 4: 85 percent / acetic acid / tetrahydrofuran; H2O / 1.5 h / 55 °C View Scheme