potassium carbonate in methanol T=25°C; 0.75 h; Yield given;

1.1: 78 percent / toluene / 3 h / 20 °C 2.1: Et3B / hexane; toluene / 2 h / 20 °C 2.2: tetra-n-butylammonium fluoride / hexane; toluene; tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / |Inert atmosphere 1.2: -78 °C / |Inert atmosphere 2.1: methanol; potassium carbonate / methanol / 20 °C / |Inert atmosphere 3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 4.1: sodium hydroxide; water / tetrahydrofuran / 0 - 20 °C View Scheme

1: 1.) PdCl2, SnCl2, (C6H5)3P / 1) acetonitrile, , 70 psi, 65 deg C, 1 h; 2) 1.5 h 2: <(C6H5)3P>3RhH(CO) / dioxane / 1.5 h / Ambient temperature View Scheme