1.1: 93 percent / thionyl chloride / CHCl3 / 0 - 20 °C 2.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 2.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 3.1: potassium hydroxide / H2O / 5 h / Heating 3.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 4.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 5.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 6.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 7.1: ozone / methanol; CH2Cl2 / -78 °C 7.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 8.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 9.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 9.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 9.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 10.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 11.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 1.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 2.1: potassium hydroxide / H2O / 5 h / Heating 2.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 3.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 4.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 5.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 6.1: ozone / methanol; CH2Cl2 / -78 °C 6.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 7.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 8.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 8.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 8.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 9.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 10.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 1.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 1.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 2.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 3.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1: COCl2; DMF / CH2Cl2; toluene / 0 - 20 °C 2: K-selrctride / tetrahydrofuran / 20 °C 3: 61 percent / tributyltin hydride; triethylborane / toluene / 72 h / 20 °C View Scheme

1: 65 percent / MnO2 / ethyl acetate / 40 h / Heating 2: 84 percent / trifluoroacetic acid / CH2Cl2 / 20 °C View Scheme

hydrogenchloride; hydrogen iodide; tin(ll) chloride 2.) MeOH, 3.) AcOH-THF; Yield given. Multistep reaction. Yields of byproduct given;

palladium on activated charcoal Heating;

sodium hydroxide; sodium tetrahydroborate in methanol; water 17 h; Heating; Yield given;

hydrogenchloride in 1,4-dioxane Heating;

1: 85 percent / 1) NaNO2, dil. HCl, 2) NaN3 / 1) 0 degC 2: 96 percent / various solvent(s) / 180 °C View Scheme