hydrogen; palladium on activated charcoal in tetrahydrofuran

1.1: AcCl 1.2: 100 percent / Et3N 2.1: 84 percent / Ph3P; hexachloroethane / CH2Cl2 / 2 h / 20 °C 3.1: 81 percent / LiBH4 / ethanol; tetrahydrofuran / 0 - 20 °C 4.1: 80 percent / Hunig's base / CH2Cl2 / 0 - 20 °C 5.1: HCl / methanol / 3 h / 20 °C 5.2: 65 percent Turnov. / CSA / benzene View Scheme

1: With hydrogenchloride in methanol T=20°C; 3 h; 2: With camphor-10-sulfonic acid in benzene T=80°C;

sodium tetrahydroborate in tetrahydrofuran 2 h;

camphor-10-sulfonic acid in benzene Heating;

tetrabutyl ammonium fluoride in tetrahydrofuran T=0°C; Overall yield = 80 percent;

1.1: 81 percent / LiBH4 / tetrahydrofuran; ethanol / 18 h / 20 °C 2.1: 95 percent / Hunig's base / CH2Cl2 / 18 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: lithium naphthalenide / tetrahydrofuran; hexane / 2 h / -78 °C 3.3: tetrahydrofuran; hexane / -78 - -40 °C 4.1: 102 mg / diethyl ether; methanol; toluene / 0 °C 5.1: HCl / methanol / 3 h / 20 °C 5.2: 50 percent / CSA / benzene / 80 °C View Scheme

1.1: 95 percent / Hunig's base / CH2Cl2 / 18 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: lithium naphthalenide / tetrahydrofuran; hexane / 2 h / -78 °C 2.3: tetrahydrofuran; hexane / -78 - -40 °C 3.1: 102 mg / diethyl ether; methanol; toluene / 0 °C 4.1: HCl / methanol / 3 h / 20 °C 4.2: 50 percent / CSA / benzene / 80 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: lithium naphthalenide / tetrahydrofuran; hexane / 2 h / -78 °C 1.3: tetrahydrofuran; hexane / -78 - -40 °C 2.1: 102 mg / diethyl ether; methanol; toluene / 0 °C 3.1: HCl / methanol / 3 h / 20 °C 3.2: 50 percent / CSA / benzene / 80 °C View Scheme

1.1: 84 percent / Ph3P; hexachloroethane / CH2Cl2 / 2 h / 20 °C 2.1: 81 percent / LiBH4 / ethanol; tetrahydrofuran / 0 - 20 °C 3.1: 80 percent / Hunig's base / CH2Cl2 / 0 - 20 °C 4.1: HCl / methanol / 3 h / 20 °C 4.2: 65 percent Turnov. / CSA / benzene View Scheme