sodium acetate; pyridinium chlorochromate in dichloromethane T=20°C; 16 h; Yield given;

molecular sieve; sodium acetate; pyridinium chlorochromate in dichloromethane T=20°C; 6 h; Title compound not separated from byproducts;

1: PCC; NaOAc; molecular sieves / CH2Cl2 / 6 h / 20 °C View Scheme

1: 3 M aq. HCl / tetrahydrofuran / 24 h / 20 °C 2: pyridinium chlorochromate, NaOAc buffer / CH2Cl2 / 12 h / 20 °C View Scheme

1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 7 h / 20 °C 2: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 18 h / Reflux View Scheme

1: tetrahydrofuran; hexane / -42 - 20 °C / Inert atmosphere 2: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 7 h / 20 °C 3: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 18 h / Reflux View Scheme

trifluorormethanesulfonic acid in 1,2-dichloro-ethane 18 h; Reflux;

1: n-butyllithium / tetrahydrofuran; hexane / -42 °C / Inert atmosphere 2: tetrahydrofuran; hexane / -42 - 20 °C / Inert atmosphere 3: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 7 h / 20 °C 4: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 18 h / Reflux View Scheme

1: diisobutylaluminium hydride / hexanes; dichloromethane / -78 °C / Inert atmosphere 2: tetrahydrofuran; hexane / -42 - 20 °C / Inert atmosphere 3: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 7 h / 20 °C 4: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 18 h / Reflux View Scheme