trimethylaluminum Yield given. Multistep reaction;

chloro-trimethyl-silane 2 h; Heating;

sodium methylate in N,N-dimethyl-formamide T=100°C; 0.25 h;

in benzene 12 h; Heating;

isopropylmagnesium chloride in tetrahydrofuran T=-10°C; 0.333333 h;

1: 72 percent / iPr2NLi / tetrahydrofuran / 2 h / -78 °C 2: 92 percent / 15percent ethanolic KOH / 48 h / Heating 3: sodium, oxalyl chloride / diethyl ether / 3 h / Heating 4: ammonia / diethyl ether / ice-cooling 5: 83 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Heating View Scheme

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 2 h / -10 °C / Industry scale 1.2: -10 - 25 °C 2.1: zinc dibromide / dichloromethane / 1.5 h / 20 - 45 °C / Industry scale 3.1: sodium hydroxide; water / methanol / 16 h / 70 °C / Industry scale 3.2: 10 °C / pH ~ 1.5 / Industry scale 4.1: Oxonereg; / dichloromethane / 24 h / 15 °C / Industry scale 5.1: triethylamine; diphenyl phosphoryl azide / toluene / 9 h / 80 °C / 760.05 Torr / Industry scale; Reflux 6.1: triethylamine / toluene; water / 7 h / 0 - 20 °C / Industry scale 7.1: benzotriazol-1-ol; 4-methyl-morpholine; N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide / acetonitrile; water / 5 h / 5 - 40 °C / Industry scale 8.1: sodium hydroxide; water / 2-methyl tetrahydrofuran / 7 h / 20 - 60 °C / Industry scale 8.2: 0.17 h / 20 - 30 °C / pH 1.5 - 3 / Industry scale 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: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 45 °C 2: pyridine / 1.5 h / 0 - 20 °C 3: sodium hydride / N,N-dimethyl-formamide / 50 °C 4: oxalyl dichloride / 0 - 20 °C 5: ammonia; potassium carbonate / dichloromethane View Scheme

lithium diisopropyl amide 1.) 30 min, -78 deg C 2.) a) ca.-100 deg C b) 5h to 10 deg C; Yield given. Multistep reaction;

methyl iodide in toluene T=95 - 115°C; 75 h;