sodium hydroxide; n-butyllithium; palladium monocarbide in tetrahydrofuran; methanol; ethanol; hexane; water; ethyl acetate

sodium hydroxide in methanol

hydrogenchloride; lithium hydroxide; hydrogen; potassium hexamethylsilazane; palladium in tetrahydrofuran; water; ethyl acetate; toluene

sodium hydroxide in ethanol

sodium hydroxide in methanol

1: 1.) NaH / 1.) EtOH, 80 deg C, 30 min, 2.) EtOH, 80 deg C, 3 h 2: 20percent aq. HCl / 16 h / Heating 3: H2, AcOH / PtO2 / methanol / 16 h / 2585.7 Torr 4: 1 N aq. NaOH / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 20percent aq. HCl / 16 h / Heating 2: H2, AcOH / PtO2 / methanol / 16 h / 2585.7 Torr 3: 1 N aq. NaOH / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: H2, AcOH / PtO2 / methanol / 16 h / 2585.7 Torr 2: 1 N aq. NaOH / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 87 percent / H2 / PtO2 / H2O; acetic acid / 72 h / 2844.3 Torr 2: Et3N / H2O; dioxane / 96 h 3: 99 percent / BH3 / tetrahydrofuran / 1 h 4: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 5: CH2Cl2 / Ambient temperature 6: 90 percent / H2 / 10percent Pd/C / ethyl acetate 7: 97 percent / NaOH / methanol View Scheme

1: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 2: CH2Cl2 / Ambient temperature 3: 90 percent / H2 / 10percent Pd/C / ethyl acetate 4: 97 percent / NaOH / methanol View Scheme