1: pyridine / 1.5 h 2: pyridine / CH2Cl2 / 1) ice-bath, 15 min; 2) 20 deg C, 3 h 3: aq. NaOH / ethanol / 1 h / 60 °C 4: 75 percent / LiEt3BH / tetrahydrofuran / 1) dry ice/acetone cooling, 1 h; 2) 20 deg C, 1 h View Scheme

1: N-methylmorpholine / acetone 2: 1N sodium hydroxide / H2O 3: 1.) AcCl, 3.) Zn, Cu / 1.) MeOH, 2.) CH2Cl2, 3.) MeOH 4: 91 percent / dimethylformamide / 6 h / 100 °C View Scheme

1: pyridine / 20 °C 2: 5 h / 0 °C 3: 3.80 g / NaOH / ethanol / 2 h / Heating View Scheme

1: 1.) pyridine / 1.) a) 0 deg C, overnight, b) 70 deg C, 3 h, 2.) a) 0 deg C, 1 h, b) RT, overnight 2: 95 percent / 1 N NaOH / ethanol / 3 h / 60 °C 3: 20 percent / LiN3 / ethanol / 2 h / Heating View Scheme

1.1: 58 percent / p-toluenesulfonic acid monohydrate / acetone / 20 °C 2.1: 86 percent / imidazole; DMAP / dimethylformamide / 20 °C 3.1: N-bromosuccinimide; benzoyl peroxide / CCl4 / Heating 4.1: 491 mg / NaHCO3 / H2O; tetrahydrofuran / 20 °C 5.1: 24 percent / imidazole; DMAP / dimethylformamide / 20 °C 6.1: AcOH / H2O / Heating 7.1: NaOH / dimethylsulfoxide; H2O / 0.33 h / 20 °C 7.2: 41 percent / dimethylsulfoxide; H2O / 1.5 h 8.1: 77 percent / AIBN; Bu3SnH / toluene / 3 h / Heating 9.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h View Scheme

1: 71 percent / pyridine / 1.25 h / Ambient temperature 2: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating 3: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h 4: 71 percent / potassium t-butoxide / CH2Cl2 / 1.5 h / Ambient temperature 5: 75 percent / diisopropylethylamine / tetrahydrofuran / 4.5 h View Scheme

in water T=20°C; pH 8.4-8.7; Rate constantEquilibrium constant;

1: N-methylmorpholine / acetone 2: 1N sodium hydroxide / H2O 3: 1.) AcCl, 3.) Zn, Cu / 1.) MeOH, 2.) CH2Cl2, 3.) MeOH 4: 91 percent / NaOH, IPA View Scheme

in water T=20°C; pH 8.4-8.7; Rate constantEquilibrium constant;