1: sodium, liquid ammonia / ethanol 2: 71 percent / 10percent aq. HCl 3: 85 percent / diethyl ether / 0.5 h 4: 1.) sodium borohydride, 2.) 10percent aq. sodium hydroxide / 1.) abs. ethanol, 1 h 5: 64 percent / zinc dust, anhydrous copper(II) chloride / diethyl ether 6: 79.5 percent / Jones reagent / acetone / 1 h 7: 92.5 percent / sodium methoxide / benzene / 13 h / Ambient temperature 8: 1.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) conc aq. HCl / 1.) benzene, room temperature, 30 min, 2.) 22 h 9: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h 10: 98 percent / toluene / 0.75 h 11: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme

1: 1.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) conc aq. HCl / 1.) benzene, room temperature, 30 min, 2.) 22 h 2: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h 3: 98 percent / toluene / 0.75 h 4: 49 percent / 10percent aq. HCl / diethyl ether / 25 h View Scheme

1: 75 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / Ambient temperature 2: HCl / H2O; ethyl acetate 3: 74 percent / potassium carbonate / dimethylformamide 4: 95 percent / KO-t-Am / toluene 5: 49 percent / aq. HCl / diethyl ether View Scheme

1: HCl / H2O; ethyl acetate 2: 74 percent / potassium carbonate / dimethylformamide 3: 95 percent / KO-t-Am / toluene 4: 49 percent / aq. HCl / diethyl ether View Scheme

1,8-diazabicyclo[5.4.0]undec-7-ene; 5-hydro-3-oxaoctafluoropentanesulfonyl fluoride in tetrahydrofuran 0.0833333 h; Inert atmosphere;

1.1: 81 percent / SnCl4 / CH2Cl2 / 20 °C 2.1: MeOK / tetrahydrofuran / 0 °C 2.2: 80 percent / K2CO3 / methanol / Heating 3.1: 63 percent / LDA / -78 - 20 °C 4.1: 76 percent / LiAlH4 / tetrahydrofuran / 20 °C 5.1: 70 percent / DDQ / benzene / 20 °C 6.1: DBU; H(CF2)2O(CF2)2SO2F / tetrahydrofuran / 0.5 h / 0 °C 6.2: 82 percent / Et3N / tetrahydrofuran / 8 h / Heating 7.1: O3 / methanol / -78 °C 7.2: 67 percent / Me2S / 20 °C 8.1: 69 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: MeOK / tetrahydrofuran / 0 °C 1.2: 80 percent / K2CO3 / methanol / Heating 2.1: 63 percent / LDA / -78 - 20 °C 3.1: 76 percent / LiAlH4 / tetrahydrofuran / 20 °C 4.1: 70 percent / DDQ / benzene / 20 °C 5.1: DBU; H(CF2)2O(CF2)2SO2F / tetrahydrofuran / 0.5 h / 0 °C 5.2: 82 percent / Et3N / tetrahydrofuran / 8 h / Heating 6.1: O3 / methanol / -78 °C 6.2: 67 percent / Me2S / 20 °C 7.1: 69 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: 63 percent / LDA / -78 - 20 °C 2.1: 76 percent / LiAlH4 / tetrahydrofuran / 20 °C 3.1: 70 percent / DDQ / benzene / 20 °C 4.1: DBU; H(CF2)2O(CF2)2SO2F / tetrahydrofuran / 0.5 h / 0 °C 4.2: 82 percent / Et3N / tetrahydrofuran / 8 h / Heating 5.1: O3 / methanol / -78 °C 5.2: 67 percent / Me2S / 20 °C 6.1: 69 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: O3 / methanol / -78 °C 1.2: 67 percent / Me2S / 20 °C 2.1: 69 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; 5-hydro-3-oxaoctafluoropentanesulfonyl fluoride / tetrahydrofuran / 0.08 h / Inert atmosphere View Scheme