hydrogen; palladium on activated charcoal in ethyl acetate P=760 Torr;

1.1: LDA / tetrahydrofuran; hexane / -78 °C 1.2: 79 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 73 percent / PtCl2 / toluene / 80 °C 3.1: 79 percent / H2 / Pd/C / ethyl acetate / 760 Torr View Scheme

1: 73 percent / PtCl2 / toluene / 80 °C 2: 79 percent / H2 / Pd/C / ethyl acetate / 760 Torr View Scheme

1.1: 88 percent / Na2CO3; LiCl / [Pd(PPh3)4] / 1,2-dimethoxy-ethane; H2O / 80 °C 2.1: LDA / tetrahydrofuran; hexane / -78 °C 2.2: 79 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 73 percent / PtCl2 / toluene / 80 °C 4.1: 79 percent / H2 / Pd/C / ethyl acetate / 760 Torr View Scheme

1.1: 88 percent / Na2CO3; LiCl / [Pd(PPh3)4] / 1,2-dimethoxy-ethane; H2O / 80 °C 2.1: LDA / tetrahydrofuran; hexane / -78 °C 2.2: 79 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 73 percent / PtCl2 / toluene / 80 °C 4.1: 79 percent / H2 / Pd/C / ethyl acetate / 760 Torr View Scheme