niobium pentachloride; zinc in tetrahydrofuran; benzene T=23°C; 3 h; Inert atmosphere;

niobium pentachloride; zinc in tetrahydrofuran; benzene T=23°C; 3 h; Inert atmosphere;

(R,R)-[Cr(salen)] hexafluoroantimonate; 4 A molecular sieve; tert-butyl alcohol in various solvent(s) T=0°C; 40 h; Title compound not separated from byproducts;

benzenesulfonamide; ethylenediaminetetraacetic acid; human soluble epoxide hydrolase in ethanol T=30°C; pH=7.4; 8 h;

1: sodium hydroxide; tri-n-butylmethylammonium chloride / water / 4 h / 60 °C / |Large scale 2: triethylamine / ethyl acetate / 0.42 h / -15 °C 3: triethylamine / ethyl acetate / 0.25 h / -15 °C 4: hydrogenchloride / water; ethyl acetate / 0.5 h / 15 - 25 °C 5: sodium hydroxide; tri-n-butylmethylammonium chloride / water / 2 h / 20 - 25 °C / |Large scale 6: ammonium hydroxide / methanol / 3 h / 40 °C / |Large scale 7: dichloromethane; isopropyl alcohol / 5 h / |Large scale 8: triethylamine; carbonic acid dimethyl ester / 0.5 h / 4 - 10 °C / |Large scale 9: potassium tert-butylate / isopropyl alcohol; tert-butyl alcohol / 1 h / 20 °C / |Large scale 10: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 10 °C / |Large scale 11: acetone / 1 h / 0 - 5 °C / |Large scale View Scheme

1: 1.) NaOH / 1.) H2O, 70 deg C; 2.) H2O, 70 deg C, 2.5 h 2: 61 percent / pyridine / 2 h / -10 °C 3: 84 percent / Et3N / CH2Cl2 / 0.5 h / 0 - 5 °C 4: 2N NaOH / dioxane / 4 h / Ambient temperature 5: 32percent NH4OH / methanol / 6 h / sealed flask 6: 98 percent / Et3N / CH2Cl2 / 0.5 h / -10 - -5 °C 7: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature 8: RED-AL / toluene / 4 h / Ambient temperature View Scheme

(R,R)-[Cr(salen)] hexafluoroantimonate; 4 A molecular sieve; tert-butyl alcohol in various solvent(s) T=0°C; 40 h; Title compound not separated from byproducts;

1: 1.) NaOH / 1.) H2O, 70 deg C; 2.) H2O, 70 deg C, 2.5 h 2: 61 percent / pyridine / 2 h / -10 °C 3: 84 percent / Et3N / CH2Cl2 / 0.5 h / 0 - 5 °C 4: 2N NaOH / dioxane / 4 h / Ambient temperature 5: 32percent NH4OH / methanol / 6 h / sealed flask 6: ethyl acetate / 16 h View Scheme

zeolite (H-ZSM 5); sodium cyanoborohydride in 1,2-dichloro-ethane 6 h; Heating; Yield givenYields of byproduct given;

in tetrahydrofuran T=0 - 20°C;