lithium bromide in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=145 - 147°C; Decarboxylation; 0.366667 h;

1: C15H24S4Si With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78°C; 1 h; Inert atmosphere; 2: dimethyl-disulfide in tetrahydrofuran; hexane T=20°C; 12 h; Inert atmosphere; 3: With tetrabutyl ammonium fluoride in tetrahydrofuran; hexane T=20°C; 1 h; Inert atmosphere;

lithium bromide in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=150°C; 0.25 h;

1: P(OEt)3 / benzene / 19.5 h / Heating 2: 65 percent / LiBr / hexamethylphosphoric acid triamide / 0.37 h / 145 - 147 °C View Scheme

1: 35 percent / trimethyl phosphite / benzene / 4 h / Heating 2: lithium bromide / hexamethylphosphoric acid triamide / 0.25 h / 150 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.08 h / -78 °C / |Inert atmosphere 1.2: 1.5 h / -78 - 20 °C / |Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere 2.2: 12 h / 20 °C / |Inert atmosphere 2.3: 1 h / 20 °C / |Inert atmosphere View Scheme

sodium methylate Yield given. Multistep reaction;

sodium ethanolate 1.) EtOH, THF, 20 deg C, 4 h, 2.) EtOH, THF, 20 deg C, 12 h; Yield given. Multistep reaction;

Yield given. Multistep reaction;