Wilkinson's catalyst in toluene T=50°C; 3 h;

1: 83 percent / Et3N / pentane 2: conc. HCl / 2 h 3: p-TsOH / tetrahydrofuran; H2O / 0.5 h View Scheme

1: 83 percent / Et3N / pentane 2: H(1+) 3: p-TsOH / methanol; tetrahydrofuran 5: Zn (dust), acetic acid / Ambient temperature 6: 76 percent View Scheme