1: 1.) sodium hydride / 1.) DMF, 1 h, 2.) DMF, overnight 2: 6 N HCl / benzene / 18 h / Heating 3: 60 percent / n-butyllithium / tetrahydrofuran; diethyl ether / 0.25 h / -95 °C View Scheme

thionyl chloride; triethylamine in benzene 2 h; Ambient temperature;

1: 78 percent / I2, Ag(OOCCF3)2 2: 87 percent / MeSO2Cl, Et3N View Scheme

1: n-BuLi, I2 / hexane; tetrahydrofuran 2: 20percent aq. HCl / methanol; benzene / 16 h 3: 97 percent / NaBH4 / propan-2-ol / 16 h / Heating 4: 87 percent / HCl / acetic acid; CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 97 percent / NaBH4 / propan-2-ol / 16 h / Heating 2: 87 percent / HCl / acetic acid; CH2Cl2 / 5 h / Ambient temperature View Scheme

1: p-TsOH / benzene / 15 h / Heating 2: n-BuLi, I2 / hexane; tetrahydrofuran 3: 20percent aq. HCl / methanol; benzene / 16 h 4: 97 percent / NaBH4 / propan-2-ol / 16 h / Heating 5: 87 percent / HCl / acetic acid; CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 20percent aq. HCl / methanol; benzene / 16 h 2: 97 percent / NaBH4 / propan-2-ol / 16 h / Heating 3: 87 percent / HCl / acetic acid; CH2Cl2 / 5 h / Ambient temperature View Scheme

1.1: 92 percent / NaI; K2CO3 / dimethylformamide / 40 - 60 °C 2.1: 95 percent / p-toluenesulfonic acid / toluene / 5 h / Heating 3.1: 95 percent / Pd(OAc)2; [Bu4N]Br; KOAc / dimethylformamide / 5 h / Heating 4.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / Heating 5.1: BH3*THF / tetrahydrofuran / 3 h / 20 °C 5.2: NaCNBH3; AcOH / 3 h / 20 °C 5.3: 75 percent / aq. NaOH; KMnO4 / CH2Cl2 / 2 h / 20 °C View Scheme