in toluene T=0°C; 0.5 h; Yield given. Yields of byproduct given;

nickel Hydrogenation;

1: 93 percent / imidazole / CH2Cl2 / 20 °C 2: 58 percent / NH4F / methanol / 3 h / 65 °C View Scheme

1: 93 percent / imidazole / CH2Cl2 / 20 °C 2: 58 percent / NH4F / methanol / 3 h / 65 °C 3: 91 percent / triphenylphosphine; DIAD / tetrahydrofuran / 20 °C 4: 96 percent / LiBEt3H / tetrahydrofuran / 2 h / -78 °C 5: 87 percent / p-TSA / 30 h / 20 °C View Scheme