sodium tetrahydroborate in tetrahydrofuran 1 h; in air;

1: isopropyl 4-hydroxy-3-iodobenzoate With methyl-magnesium chloride in tetrahydrofuran T=-10°C; 0.25 h; 2: With isopropylmagnesium chloride in tetrahydrofuran T=-10°C; 2.5 h; 3: 2,2-dimethyl-cyclopentanone Further stages;

1: methyl 3-Iodo-4-hydroxybenzoate With methyl-magnesium chloride; lithium iso-propoxide in tetrahydrofuran T=-25°C; 1.41667 h; 2: With isopropylmagnesium chloride in tetrahydrofuran T=-25°C; 2.16667 h; 3: 2,2-dimethyl-cyclopentanone Further stages;

hydroxylamine-o-sulphonic acid T=15 - 100°C;

CF3CO3H T=0°C;

T=65°C;

T=65°C;

1: With ammonium formate T=145°C; 2: With hydrogenchloride in methanol Further stages.;

iodine T=110°C; Hantzsch type reaction; 2.5 h; neat (no solvent);

1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane / 1 h / -78 °C 2.1: tetrahydrofuran / -78 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium phenolate / toluene / 2 h / 50 °C / |Inert atmosphere 4.1: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; potassium phosphate / N,N-dimethyl-formamide; water / 21 h / 75 °C / |Inert atmosphere 5.1: pyridinium p-toluenesulfonate / methanol / 19 h / 50 °C 6.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0.33 h 6.2: 3 h / 20 °C 7.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 90 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 3.5 h / 0 - 40 °C 9.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 - 20 °C 10.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 11.1: lithium hydroxide hydrate / tetrahydrofuran; methanol / 20 °C View Scheme