oxygen; 1-n-butyl-3-methylimidazolium tetrafluoroborate; copper(l) chloride; palladium dichloride in water T=60°C; Wacker oxidation; 58 h;

1: With borane-pyridine complex in dichloromethane T=20°C; 2: With sodium hydroxide; dihydrogen peroxide in methanol; dichloromethane T=0 - 20°C;

Mo(CHCMe2Ph)(NAr)lt;OCMe(CF3)2gt;2 (Schrock's molybdenum catalyst) in ethylene glycol dimethyl ether 4 h; Yields of byproduct given;

1H-imidazole in N,N-dimethyl-formamide

RuCl(Ph3P)3; triphenylphosphine in tetrahydrofuran; isopropyl alcohol T=25°C; 7 h;

1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane in tetrahydrofuran T=25°C; 1 h; 2: 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]pentanal in tetrahydrofuran T=25°C; Wittig reaction; 7 h;

1: HO(CH2)5OTBS With 1,10-phenanthroline; potassium tert-butylate; copper(l) chloride in o-di-fluorobenzene T=20°C; 0.166667 h; Inert atmosphere; 2: With 1-methyl-1H-imidazole; di-tert-butylazodicarboxylate; oxygen in o-di-fluorobenzene Reflux; 3: diazomethyl-trimethyl-silane With triphenylphosphine; isopropyl alcohol in o-di-fluorobenzene; diethyl ether T=60°C; Inert atmosphere;

Schwartz's reagent in toluene T=20°C; Hydrogenation; 12 h;

sodium chloride in ethyl acetate; N,N-dimethyl-formamide

1: Bu4NOAc; Pd(IiPr)(OAc)2*(H2O); O2 / toluene / 12 h / 60 °C 2: 38 mg / PPh3; RhCl(PPh3)3 / toluene; dioxane; propan-2-ol / 50 °C View Scheme