1: diethyl ether / 20 °C 2: 1.17 g / pyridinium chlorochromate / CH2Cl2 View Scheme

chromium(VI) oxide; aluminum oxide 1.) 0 deg C to r.t., 20 h; 2.) 0 deg C, 20 h; Yield givenMultistep reaction;

1: 98.9 percent / morpholine / ethanol / 4 h / Heating 2: 96.8 percent / 100percent H3PO4 / 0.33 h / Heating View Scheme

tin; hydrogen bromide in diethyl ether T=20°C;

titanium tetrachloride in dichloromethane -78 deg C, 2 h -> 0 deg C;

1.1: pyridine / 60 h / 5 - 35 °C / Industry scale 1.2: 30 °C / Industry scale 2.1: sulfuric acid / n-heptane / 18 h / 19 - 25 °C / Industry scale; Sealed vessel 3.1: n-hexyl lithium / n-heptane; tetrahydrofuran / 0.5 h / -65 - -55 °C / Industry scale 3.2: 1.5 h / -65 - -55 °C / Industry scale 4.1: (+)-CSO / n-heptane; tetrahydrofuran / 6 h / -65 - -55 °C / Industry scale 4.2: -60 - -40 °C / Industry scale 5.1: trifluoroacetic acid / toluene / 25.5 h / 50 °C / Industry scale 5.2: 15 - 20 °C / pH 5 - 6 / Industry scale 6.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / 2-methyl tetrahydrofuran / 0.08 h / 0 - 10 °C / Industry scale 6.2: 4 h / 0 - 35 °C / Industry scale 7.1: hydrogen; acetic acid / palladium on carbon / methanol / 7 h / 60 °C / 4137.29 Torr / Industry scale 8.1: hydrogenchloride / water; tert-butyl methyl ether / 3 °C / Industry scale; Reflux 9.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide / ethyl acetate; acetonitrile; water / -5 - 30 °C / Industry scale 10.1: sodium acetate; sodium hypochlorite; acetic acid; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / methyl acetate; water; tert-butyl methyl ether / 2 h / 5 - 15 °C / Industry scale View Scheme

1: 1.) Mg / 1.) diethyl ether, 15 min, reflux, 2.) 10 min 2: 3 N chromic acid / acetone / 1 h / 45 °C 3: potassium tert-butoxide / tetrahydrofuran / 18 h / -78 °C View Scheme

tin; hydrogen bromide in ethanol; water 4 h; Ambient temperature;

tin in ethanol; water 10 h; Ambient temperature; Yield given. Yields of byproduct given;

hydrogen in methanol T=25°C; P=2068.65 Torr; 8 h; Inert atmosphere;