sodium ethanolate in ethanol 24 h; Heating;

AlCl3, aluminium chloride in nitromethane T=60°C; 0.5 h; Acidic conditionsMicrowave irradiation;

sodium hydroxide; sodium dithionite T=90°C; 5 h;

1: 44 mg / pyridinium chlorochromate / CH2Cl2 / 2 h 2: 24 mg / 1 percent aq. NaOH, 5 percent aq Na2S2O4 / 5 h / 90 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / |Inert atmosphere 1.2: 12 h / -78 °C / |Inert atmosphere 1.3: 2 h / -78 °C / |Inert atmosphere 2.1: potassium hexacyanoferrate(III); methanesulfonamide; K2OsO4*2H2O; sodium hydrogencarbonate; potassium carbonate; (DHQD)2Pyr / water; tert-butyl alcohol / 72 h / 0 °C 3.1: sulfuric acid / 3 h / 80 °C 4.1: tetrahydrofuran / 1 h / -78 - -70 °C 5.1: hydrogenchloride / methanol / 14 h / 20 °C 6.1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / 0.75 h / |Reflux 7.1: silver perchlorate / tetrahydrofuran / 20 °C / |Inert atmosphere 8.1: toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 0 - 20 °C 9.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 9.2: -78 - 20 °C / |Inert atmosphere 10.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 11.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

1.1: tetrahydrofuran / 1 h / -78 - -70 °C 2.1: hydrogenchloride / methanol / 14 h / 20 °C 3.1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / 0.75 h / |Reflux 4.1: silver perchlorate / tetrahydrofuran / 20 °C / |Inert atmosphere 5.1: toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 0 - 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 6.2: -78 - 20 °C / |Inert atmosphere 7.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 8.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

1.1: toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 4.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

1.1: potassium hexacyanoferrate(III); methanesulfonamide; K2OsO4*2H2O; sodium hydrogencarbonate; potassium carbonate; (DHQD)2Pyr / water; tert-butyl alcohol / 72 h / 0 °C 2.1: sulfuric acid / 3 h / 80 °C 3.1: tetrahydrofuran / 1 h / -78 - -70 °C 4.1: hydrogenchloride / methanol / 14 h / 20 °C 5.1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / 0.75 h / |Reflux 6.1: silver perchlorate / tetrahydrofuran / 20 °C / |Inert atmosphere 7.1: toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 0 - 20 °C 8.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 8.2: -78 - 20 °C / |Inert atmosphere 9.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 10.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 1.2: -78 - 20 °C / |Inert atmosphere 2.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 3.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 2: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme