sodium tetrahydroborate; acetic acid in ethanol; water pH=4.5; 0.5 h; Inert atmosphere;

sodium tetrahydroborate; acetic acid 1.) ethanol, 30 min, 2.) pH 5.0, water, room temperature, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

hydrogenchloride Ambient temperature;

hydrogenchloride 0.5 h;

sodium tetrahydroborate; acetic acid 1.) ethanol, 30 min, 2.) pH 5.0, water, room temperature, 1 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

1.1: 81 percent / K2CO3 / dimethylformamide / 0 - 20 °C 2.1: 88 percent / N-bromosuccinimide / CH2Cl2 / -78 - 20 °C 3.1: DDQ / CH2Cl2 / 3.5 h / 20 °C 3.2: 45 percent / DMAP / CH2Cl2 / 0.25 h 4.1: 53 percent / TiCl4 / CH2Cl2; tetrahydrofuran / 5 h / 20 °C 5.1: 100 percent / H2; Et3N; NaHCO3 / Pd(OH)2/C / H2O; methanol; ethyl acetate / 18 h / 20 °C View Scheme

1.1: 79 percent / K2CO3 / acetone / 6 h / Heating 2.1: NaH / dimethylformamide / 0.25 h / 10 °C 2.2: 88 percent / dimethylformamide / 0.33 h / 20 °C 3.1: 80 percent / Bu3SnH; AIBN / toluene / 8.25 h / Heating 4.1: 87 percent / NBS / CH2Cl2 / 1.83 h / -70 - -16 °C 5.1: t-BuLi / tetrahydrofuran; pentane / 0.07 h / -78 °C 5.2: tetrahydrofuran; pentane / 1.67 h / -78 - -10 °C 5.3: H2 / Pd(OH)2/C / methanol; ethyl acetate / 6 h / 20 °C / 750.08 Torr 6.1: NaIO4; RuCl3*xH2O / CCl4; acetonitrile; H2O / 2 h / 20 °C 6.2: tetrahydrofuran; methanol / 65 h / 20 °C View Scheme

MgCl2*6H2O T=35°C; 20 h;

in water 96 h;

phosphate-citrate buffer; dihydrogen peroxide; horseradish peroxidase in water; acetone pH=5.0; 0.75 h;