potassium carbonate in N,N-dimethyl-formamide T=150°C; 1.5 h;

potassium carbonate in acetone

1: 89 percent / pyridine / 20 °C 2: potassium carbonate / acetone / Heating 3: 97.4 g / sodium methoxide / methanol / 3 h / 20 °C 4: 81 percent / potassium carbonate / butan-2-one / 2.5 h / Heating View Scheme

1: 97.4 g / sodium methoxide / methanol / 3 h / 20 °C 2: 81 percent / potassium carbonate / butan-2-one / 2.5 h / Heating View Scheme

1: HCl 2: NaOH 3: K2CO3 / KI View Scheme

1: potassium carbonate / acetone / Heating 2: 97.4 g / sodium methoxide / methanol / 3 h / 20 °C 3: 81 percent / potassium carbonate / butan-2-one / 2.5 h / Heating View Scheme

1: potassium carbonate / acetonitrile / 4 h / 40 °C 2: potassium carbonate; water / methanol / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 110 °C View Scheme

1.1: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 2.1: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 3.1: dioxane / 24 h / 20 °C 3.2: 64 percent / HCl / dioxane / 24 h / 20 °C 4.1: 94 percent / pyridine / 0.25 h / 0 °C 5.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 6.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 7.1: 83 percent / pyridine / 3 h / 0 °C 8.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 9.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 10.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 11.1: NaBH4 / methanol / 24 h / 20 °C View Scheme

1.1: N-bromosuccinmide / N,N-dimethyl-formamide / 16 h / 20 °C 2.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 3.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 3.2: 16 h / 20 °C 4.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 5.2: 0 - 20 °C 6.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 2.1: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C 3.1: dioxane / 24 h / 20 °C 3.2: 64 percent / HCl / dioxane / 24 h / 20 °C 4.1: 94 percent / pyridine / 0.25 h / 0 °C 5.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 6.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 7.1: 83 percent / pyridine / 3 h / 0 °C 8.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 9.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 10.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 11.1: NaBH4 / methanol / 24 h / 20 °C 12.1: 46.3 mg / 48 h / Heating 13.1: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme