1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran T=-78°C; 0.5 h; Inert atmosphere; 2: phenoxyacetic acid methyl ester in tetrahydrofuran T=-78 - 20°C; 2.5 h; Inert atmosphere;

n-butyllithium in tetrahydrofuran; hexane

n-butyllithium in tetrahydrofuran; hexane

in tetrahydrofuran; hexane

in tetrahydrofuran; hexane; water

in tetrahydrofuran T=-78°C;

1.1: potassium carbonate / acetone / 16 h / 25 - 56 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 2.5 h / -78 - 20 °C / Inert atmosphere View Scheme

1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C 3: K2CO3 / methanol / 3 h / 20 °C 4: 83 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C 5: NaN(SiMe3)2 / tetrahydrofuran / 3 h / 0 °C View Scheme

1: NaH 2: morpholinosulfur trifluoride / CHCl3 / 82 h / 30 - 40 °C View Scheme

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h 2: 36 percent / NaBH4 / methanol; tetrahydrofuran / -45 °C 3: K2CO3 / methanol / 1 h / 50 °C 4: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min View Scheme