1: With lithium triethylborohydride in tetrahydrofuran T=-78°C; 0.75 h; 2: With tetrabutyl ammonium fluoride in tetrahydrofuran T=23°C; 12 h;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C 2.1: LDA / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 3.1: LDA / tetrahydrofuran; hexane / 3 h / -78 - 23 °C 4.1: aq. NH4Cl / tetrahydrofuran; hexane / 23 °C 5.1: 90 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH2Cl2 / 3 h / 23 °C 6.1: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 23 °C 7.1: LiEt3BH / tetrahydrofuran / 0.75 h / -78 °C 7.2: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 23 °C View Scheme

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 2.1: LDA / tetrahydrofuran; hexane / 3 h / -78 - 23 °C 3.1: aq. NH4Cl / tetrahydrofuran; hexane / 23 °C 4.1: 90 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH2Cl2 / 3 h / 23 °C 5.1: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 23 °C 6.1: LiEt3BH / tetrahydrofuran / 0.75 h / -78 °C 6.2: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 23 °C View Scheme

1.1: 90 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH2Cl2 / 3 h / 23 °C 2.1: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 23 °C 3.1: LiEt3BH / tetrahydrofuran / 0.75 h / -78 °C 3.2: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 23 °C View Scheme

1.1: 97 percent / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 23 °C 2.1: LiEt3BH / tetrahydrofuran / 0.75 h / -78 °C 2.2: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 23 °C View Scheme

1: 82 percent / p-toluene sulfonic acid / benzene / 3 h / Heating 2: LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 10percent aq. HCl / 1 h / Ambient temperature 4: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme

1: LiAlH4 / tetrahydrofuran / 3 h / Heating 2: 10percent aq. HCl / 1 h / Ambient temperature 3: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme

1: 30 percent / 40percent benzyltrimethylammonium hydroxide in MeOH / dioxane / 0 - 20 °C 2: 82 percent / p-toluene sulfonic acid / benzene / 3 h / Heating 3: LiAlH4 / tetrahydrofuran / 3 h / Heating 4: 10percent aq. HCl / 1 h / Ambient temperature 5: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme

1: 10percent aq. HCl / 1 h / Ambient temperature 2: 10percent aq. NaOH / 1 h / Ambient temperature; pH = 9 View Scheme

hydrogen; palladium on activated charcoal in ethanol P=2327.2 Torr; 3 h;