cyclohexa-1,4-diene; palladium on activated charcoal in ethanol; N,N-dimethyl-formamide T=40°C; Hydrogenolysis; 10 h;

1: 72 percent / silver carbonate; molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 20 °C 2: 94 percent / sodium methoxide / methanol / 2 h / 20 °C 3: 86 percent / pyridine / 0 - 20 °C 4: 92 percent / pyridine / 0 - 20 °C 5: 79 percent / AcOH / dioxane / 6 h / 110 °C 6: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 7: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 8: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 9: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 10: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 2: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 3: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 4: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 5: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 100 percent / α,α-dichloromethyl methyl ether; ZnCl2*Et2O / CH2Cl2 / 1 h / 20 °C 2: 72 percent / silver carbonate; molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 20 °C 3: 94 percent / sodium methoxide / methanol / 2 h / 20 °C 4: 86 percent / pyridine / 0 - 20 °C 5: 92 percent / pyridine / 0 - 20 °C 6: 79 percent / AcOH / dioxane / 6 h / 110 °C 7: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 8: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 9: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 10: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 11: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 72 percent / silver carbonate; molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 20 °C 2: 94 percent / sodium methoxide / methanol / 2 h / 20 °C 3: 86 percent / pyridine / 0 - 20 °C 4: 92 percent / pyridine / 0 - 20 °C 5: 79 percent / AcOH / dioxane / 6 h / 110 °C 6: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 7: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 8: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 9: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 10: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 86 percent / pyridine / 0 - 20 °C 2: 92 percent / pyridine / 0 - 20 °C 3: 79 percent / AcOH / dioxane / 6 h / 110 °C 4: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 5: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 6: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 7: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 8: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 2: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 3: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 4: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 5: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 94 percent / sodium methoxide / methanol / 2 h / 20 °C 2: 86 percent / pyridine / 0 - 20 °C 3: 92 percent / pyridine / 0 - 20 °C 4: 79 percent / AcOH / dioxane / 6 h / 110 °C 5: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 6: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 7: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 8: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 9: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 92 percent / pyridine / 0 - 20 °C 2: 79 percent / AcOH / dioxane / 6 h / 110 °C 3: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 4: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 5: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 6: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 7: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme

1: 79 percent / AcOH / dioxane / 6 h / 110 °C 2: 79 percent / DCC; DMAP; DMAP*HCl / CH2Cl2 / Heating 3: 66 percent / selenium dioxide; AcOH / dioxane / 3 h / 80 °C 4: 73 percent / boron trifluoride diethyl etherate / CH2Cl2 / 5 h / -20 °C 5: 49 percent / methylamine / CH2Cl2; methanol / 9 h / -20 °C 6: 44 percent / 1,4-cyclohexadiene / Pd/C / dimethylformamide; ethanol / 10 h / 40 °C View Scheme