sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate T=80 - 85°C; pH=14; 31 h;

tetrabutylammomium bromide in dichloromethane; water

(i) NaOH, EtOH, (ii) aq. HBr, H2SO4; Multistep reaction;

1.1: potassium carbonate; sodium iodide / tetrahydrofuran / 16 h / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.67 h / -15 °C 3.1: tetrahydrofuran / 16 h / -15 - 20 °C 4.1: tetrahydrofuran / 2 h / -78 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); N,N'-dimethyl-barbituric acid / dichloromethane / 3 h / 35 °C 6.1: benzoic acid / toluene / 16 h / 80 °C 7.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 7.2: 16 h / 0 - 20 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 60 °C 9.1: Pearlman's catalist; hydrogen / methanol / 16 h / 20 °C 10.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran 10.2: 16 h / 20 °C View Scheme

1.1: potassium carbonate; sodium iodide / tetrahydrofuran / 16 h / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.67 h / -15 °C 3.1: tetrahydrofuran / 16 h / -15 - 20 °C 4.1: tetrahydrofuran / 2 h / -78 °C 4.2: 12 h / -78 - 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0); N,N'-dimethyl-barbituric acid / dichloromethane / 3 h / 35 °C 6.1: benzoic acid / toluene / 16 h / 80 °C 7.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C 7.2: 16 h / 0 - 20 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 60 °C 9.1: Pearlman's catalist; hydrogen / methanol / 16 h / 20 °C 10.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran 10.2: 16 h / 20 °C View Scheme

in ethanol T=20°C; 12 h;

1: K2CO3 / acetonitrile / Heating 2: 45 percent HBr View Scheme

potassium carbonate in ethanol T=70°C; 8 h;