hydrogen; palladium on activated charcoal in methanol P=2250.2 Torr; 4 h; Ambient temperature;

hydrogenchloride; zinc in tetrahydrofuran 3 h; Heating;

1: 42 percent / 1.6 M nBuLi / hexane; tetrahydrofuran / 4 h / -78 °C 2: 72 percent / Zn, 2 N HCl / tetrahydrofuran / 3 h / Heating View Scheme

1: 42 percent / 1.6 M nBuLi / hexane; tetrahydrofuran / 4 h / -78 °C 2: 72 percent / Zn, 2 N HCl / tetrahydrofuran / 3 h / Heating View Scheme

1: 27.9 percent / TsOH / methanol / 1) reflux, 5 h, 2) r.t., 72 h 2: 36.7 percent / H2 / 10percent Pd/C / methanol / 4 h / 2250.2 Torr / Ambient temperature View Scheme

1.1: 79 percent / methanesulfonyl chloride; Et3N / CH2Cl2 / 8 h / 0 °C 2.1: Mg / diethyl ether / 0.17 h / Heating 2.2: 64 percent / diethyl ether / 18 h / 20 °C 3.1: 67 percent / Zn; aq. HCl / tetrahydrofuran / 5 h / Heating View Scheme

1.1: 79 percent / KOH / methanol; H2O / 7 h / 0 °C 2.1: 79 percent / methanesulfonyl chloride; Et3N / CH2Cl2 / 8 h / 0 °C 3.1: Mg / diethyl ether / 0.17 h / Heating 3.2: 64 percent / diethyl ether / 18 h / 20 °C 4.1: 67 percent / Zn; aq. HCl / tetrahydrofuran / 5 h / Heating View Scheme