sodium hydroxide in 1,4-dioxane; water T=80°C; 2 h;

1: 63 percent / POCl3 / 1) 0 deg C, 20 min, 2) 65 deg C, 10 h 2: 79 percent / NaOH / H2O; dioxane / 2 h / 80 °C View Scheme

1: 82 percent / K2CO3, Bu4NI / H2O; tetrahydrofuran / 10 h / 80 °C 2: 63 percent / POCl3 / 1) 0 deg C, 20 min, 2) 65 deg C, 10 h 3: 79 percent / NaOH / H2O; dioxane / 2 h / 80 °C View Scheme

1: 82 percent / K2CO3, Bu4NI / H2O; tetrahydrofuran / 10 h / 80 °C 2: 63 percent / POCl3 / 1) 0 deg C, 20 min, 2) 65 deg C, 10 h 3: 79 percent / NaOH / H2O; dioxane / 2 h / 80 °C View Scheme

1: triphenylphosphine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 2: ethylmagnesium bromide / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 4 h / -78 - 20 °C 2.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme