1.1: 82 percent / K2CO3; LiCl / Pd(OAc)2 / dimethylformamide / 72 h / 100 °C 2.1: 91 percent / aq. HCl / tetrahydrofuran 3.1: NaOH / ethanol 3.2: triphosgene / tetrahydrofuran / 45 °C 3.3: 84 percent / HCl / diethyl ether / 24 h 4.1: 85 percent / Cs2CO3 / dimethylformamide; tetrahydrofuran / 20 °C 5.1: CH3COOH / CH2Cl2 / 24 h 5.2: 90 percent / TFA / CH2Cl2 / 0.5 h 6.1: PhSH; NaH / 1,2-dimethoxy-ethane / 8 h / 20 °C 6.2: m-CPBA / CH2Cl2 / -78 °C 6.3: 64 percent / Na2CO3 / toluene / Heating 7.1: 75 percent / Ni(COD)2 / acetonitrile / 0.5 h / 20 °C 8.1: 70 percent / H2 / Crabtree's catalyst / 760.05 Torr 9.1: DMAP / tetrahydrofuran / 91 h View Scheme

1: 85 percent / CuI, Pd(PPh3)2Cl2 / triethylamine / 24 h / 80 °C 2: 70 percent / t-BuOK / 2-methyl-propan-2-ol / 5 h / Heating View Scheme

1: 271 mg / diisopropylethylamine,; benzyltriethylammonium chloride,; palladium(II) acetate / dimethylformamide / 19 h / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 4: 82 percent / benzene; hexane / 0.83 h / Heating 5: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating 6: 68 percent / boron tribromide / CH2Cl2 / 9 h / 20 °C View Scheme

trifluoroacetic acid in dichloromethane

1: 271 mg / diisopropylethylamine,; benzyltriethylammonium chloride,; palladium(II) acetate / dimethylformamide / 19 h / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 4: 82 percent / benzene; hexane / 0.83 h / Heating 5: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating View Scheme