hydrogen; palladium dihydroxide in methanol T=20°C; 2 h;

toluene-4-sulfonic acid in methanol

1.1: 8.64 g / triethylamine / diethyl ether / 1 h / cooling 2.1: 9.15 g / NaI / acetone / 2 h / Heating 3.1: Mg / tetrahydrofuran 3.2: CuI / tetrahydrofuran 3.3: 35 percent / 4-methylbenzenesulfonic acid / ethanol / Heating 4.1: 90 percent / H2 / Pd(OH)2/C / methanol / 2 h / 20 °C View Scheme

1.1: Mg / tetrahydrofuran 1.2: CuI / tetrahydrofuran 1.3: 35 percent / 4-methylbenzenesulfonic acid / ethanol / Heating 2.1: 90 percent / H2 / Pd(OH)2/C / methanol / 2 h / 20 °C View Scheme

1.1: 9.15 g / NaI / acetone / 2 h / Heating 2.1: Mg / tetrahydrofuran 2.2: CuI / tetrahydrofuran 2.3: 35 percent / 4-methylbenzenesulfonic acid / ethanol / Heating 3.1: 90 percent / H2 / Pd(OH)2/C / methanol / 2 h / 20 °C View Scheme

1: 91 percent / CuLi2Cl4 / tetrahydrofuran; diethyl ether / 0 °C 2: 80 percent / p-toluenesulfonic acid monohydrate / methanol View Scheme

1: 92 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran / 4 h / Ambient temperature 2: 91 percent / CuLi2Cl4 / tetrahydrofuran; diethyl ether / 0 °C 3: 80 percent / p-toluenesulfonic acid monohydrate / methanol View Scheme

dipyridinium dichromate in dichloromethane 18 h; Ambient temperature;