sodium triphenoxide in dimethyl sulfoxide

in acetone 48 h; Darkness;

1.1: toluene-4-sulfonic acid / ethanol / 1.5 h / Reflux 2.1: trichlorophosphate / 1,2-dichloro-benzene / 1.5 h / 20 °C 2.2: 4 h / 105 °C 2.3: 20 °C 3.1: 3 h / 115 °C / Inert atmosphere 3.2: 1 h / 20 °C / Molecular sieve; Inert atmosphere 4.1: sodium carbonate; p-toluenesulfonyl chloride / tetrahydrofuran; water / 2 h / 20 °C 4.2: 12 h 4.3: 0 °C / pH 10 5.1: acetone / 48 h / Darkness View Scheme

1.1: trichlorophosphate / 1,2-dichloro-benzene / 1.5 h / 20 °C 1.2: 4 h / 105 °C 1.3: 20 °C 2.1: 3 h / 115 °C / Inert atmosphere 2.2: 1 h / 20 °C / Molecular sieve; Inert atmosphere 3.1: sodium carbonate; p-toluenesulfonyl chloride / tetrahydrofuran; water / 2 h / 20 °C 3.2: 12 h 3.3: 0 °C / pH 10 4.1: acetone / 48 h / Darkness View Scheme

1.1: 3 h / 115 °C / Inert atmosphere 1.2: 1 h / 20 °C / Molecular sieve; Inert atmosphere 2.1: sodium carbonate; p-toluenesulfonyl chloride / tetrahydrofuran; water / 2 h / 20 °C 2.2: 12 h 2.3: 0 °C / pH 10 3.1: acetone / 48 h / Darkness View Scheme

1.1: sodium carbonate; p-toluenesulfonyl chloride / tetrahydrofuran; water / 2 h / 20 °C 1.2: 12 h 1.3: 0 °C / pH 10 2.1: acetone / 48 h / Darkness View Scheme

nicotinate 11; sodium bis(2-methoxyethoxy)aluminium dihydride 1.) xylene, 130 deg C, 2.) methanol; Yield given. Multistep reaction;

2: 1.) Vitride, 2.) nicotinate 11 / 1.) xylene, 130 deg C, 2.) methanol View Scheme