lithium bromide in acetone 12 h; Inert atmosphereReflux;

1: potassium hydroxide / diethyl ether / 12 h / 20 °C 2: diazomethyl-trimethyl-silane / methanol; tetrahydrofuran / 0 °C / |Inert atmosphere 3: pyridine; p-toluenesulfonyl chloride / chloroform / 0 - 20 °C / |Inert atmosphere 4: lithium bromide / acetone / 5 h / |Inert atmosphere; |Reflux View Scheme

1: selenium(IV) oxide / anhydrous xylene / 44 h / 140 °C 2: potassium hydroxide / diethyl ether / 12 h / 20 °C 3: diazomethyl-trimethyl-silane / methanol; tetrahydrofuran / 0 °C / |Inert atmosphere 4: pyridine; p-toluenesulfonyl chloride / chloroform / 0 - 20 °C / |Inert atmosphere 5: lithium bromide / acetone / 5 h / |Inert atmosphere; |Reflux View Scheme

1: diazomethyl-trimethyl-silane / methanol; tetrahydrofuran / 0 °C / |Inert atmosphere 2: pyridine; p-toluenesulfonyl chloride / chloroform / 0 - 20 °C / |Inert atmosphere 3: lithium bromide / acetone / 5 h / |Inert atmosphere; |Reflux View Scheme

1: 94 percent / sodium azide / dimethylsulfoxide / 6 h / 20 °C 2: 89 percent / NaOH / methanol; H2O / 15 h / 20 °C 3: 94 percent / SOCl2 / 1 h / Heating 4: 87 percent / tri-n-butylstannane; AIBN / benzene / Heating View Scheme

1: (bis-methylsulfanyl-methyl)-trimethyl-silane With n-butyllithium in tetrahydrofuran; hexane T=-78°C; Inert atmosphere; 2: methyl 2-(2-bromoethyl)benzoate in tetrahydrofuran; hexane T=-78 - 20°C; Inert atmosphere; 3: With tetrabutyl ammonium fluoride; water; 1,1,1,3,3,3-hexamethyl-disilazane in tetrahydrofuran T=-78 - 20°C; Inert atmosphere;

1: (bis-methylsulfanyl-methyl)-trimethyl-silane With n-butyllithium in tetrahydrofuran; hexane T=-78°C; Inert atmosphere; 2: methyl 2-(2-bromoethyl)benzoate in tetrahydrofuran; hexane T=-78 - 20°C; Inert atmosphere;