potassium tert-butylate in tetrahydrofuran 0.0833333 h;

iodine Destillation;

1: sodium hydride / tetrahydrofuran / 1 h / 25 °C 2: 80percent m-chloroperbenzoic acid / CH2Cl2 / 25 °C 3: 1.) hexamethylphosphoric triamide (HMPA), n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to 25 deg C 4: 1.) hexamethylphosphoric triamide (HMPA), n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) from -78 deg C to RT, 4 h 5: 82 percent / acetone; H2O / 20 h / Ambient temperature 6: tetra-n-butylammonium fluoride ((TBA)F), 4-Angstroem molecular sieves / tetrahydrofuran / -78 - 25 °C 7: 87percent m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 1 h / 25 °C 8: 93 percent / t-BuOK / tetrahydrofuran / 0.08 h View Scheme

1: 80percent m-chloroperbenzoic acid / CH2Cl2 / 25 °C 2: 1.) hexamethylphosphoric triamide (HMPA), n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to 25 deg C 3: 1.) hexamethylphosphoric triamide (HMPA), n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) from -78 deg C to RT, 4 h 4: 82 percent / acetone; H2O / 20 h / Ambient temperature 5: tetra-n-butylammonium fluoride ((TBA)F), 4-Angstroem molecular sieves / tetrahydrofuran / -78 - 25 °C 6: 87percent m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 1 h / 25 °C 7: 93 percent / t-BuOK / tetrahydrofuran / 0.08 h View Scheme

1: diethyl ether 2: SnCl4; carbon disulfide / 0 °C View Scheme

2: toluene-4-sulfonic acid View Scheme

2: toluene-4-sulfonic acid View Scheme

dimethylsulfide; boron trifluoride diethyl etherate; ClIMg 1.) Et2O; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2,6-di-tert-butyl-pyridine; copper(l) chloride in dichloromethane T=70°C; 24 h; Inert atmosphere;

1: diethyl ether 2: aqueous H2SO4 View Scheme