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potassium carbonate in N,N-dimethyl-formamide T=20°C;

1: potassium carbonate; potassium iodide / ethanol / 24 h / |Reflux 2: trichlorophosphate / 19 h / 100 - 115 °C / |Cooling with ice View Scheme

trichlorophosphate T=100 - 115°C; Vilsmeier-Haack Formylation; 19 h; Cooling with ice; Overall yield = 84.4 percent; Overall yield = 6.5 g;

ethanol

potassium permanganate

AlCl3, aluminium chloride in dichloromethane T=20°C; 5 h;

1: 80 percent / m-CPBA, KHCO3 / CH2Cl2 / 3 h / Ambient temperature 2: 93 percent / AlCl3 / CH2Cl2 / 6 h / Ambient temperature 3: 73 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: 91 percent / K2CO3 / methanol / 2 h / Ambient temperature 5: 34 percent / K2CO3 / dimethylformamide / 24 h / 100 °C 6: 24 percent / AlCl3 / CH2Cl2 / 3 h / Ambient temperature View Scheme

1.1: titanium(IV) isopropylate; triethylamine / ethanol / 16 h / 30 °C 1.2: 14 h 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -10 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: palladium 10 on activated carbon; hydrogen / methanol / 8 h / 20 °C / 760.05 Torr 4.1: water / ethanol / 4 h / Reflux 5.1: oxalyl dichloride / 2 h / Reflux 6.1: ammonium hydroxide / diethyl ether / 1 h / 0 - 20 °C 7.1: 2,4,6-trichloro-1,3,5-triazine / N,N-dimethyl-formamide / 16 h / 20 °C 8.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 8.2: 0.67 h / -78 - -60 °C / Inert atmosphere 9.1: hydrogenchloride; water / methanol / 2 h / 20 °C 10.1: potassium hydroxide / ethanol; water / 12 h / Reflux 11.1: pyridine / 20 °C 12.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C 13.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Inert atmosphere; Reflux 14.1: boron trichloride / dichloromethane / -78 - 20 °C / Inert atmosphere View Scheme

1.1: titanium(IV) isopropylate; triethylamine / ethanol / 16 h / 30 °C 1.2: 14 h 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -10 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: palladium 10 on activated carbon; hydrogen / methanol / 8 h / 20 °C / 760.05 Torr 4.1: water / ethanol / 4 h / Reflux 5.1: oxalyl dichloride / 2 h / Reflux 6.1: ammonium hydroxide / diethyl ether / 1 h / 0 - 20 °C 7.1: 2,4,6-trichloro-1,3,5-triazine / N,N-dimethyl-formamide / 16 h / 20 °C 8.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 8.2: 0.67 h / -78 - -60 °C / Inert atmosphere 9.1: hydrogenchloride; water / methanol / 2 h / 20 °C 10.1: potassium hydroxide / ethanol; water / 12 h / Reflux 11.1: pyridine / 20 °C 12.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C 13.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Inert atmosphere; Reflux 14.1: boron trichloride / dichloromethane / -78 - 20 °C / Inert atmosphere View Scheme