lithium hydroxide in water; isopropyl alcohol

1: 1.) KBr, 2.) t-BuOOH, vanadyl acetylacetonate / 1.) AcOH-H2O-THF, 5 deg C, 12 h, 2.) benzene, 23 deg C, 130 min 2: K2CO3 / methanol 3: saponification 4: MICA 5: potassium selenocyanate / methanol / Heating View Scheme

1: K2CO3 / methanol 2: saponification 3: MICA 4: potassium selenocyanate / methanol / Heating View Scheme

KSeCN in methanol Heating; Yield given;

1: MICA 2: potassium selenocyanate / methanol / Heating View Scheme

1: saponification 2: MICA 3: potassium selenocyanate / methanol / Heating View Scheme

1: 100 percent / LiOH / H2O; 1,2-dimethoxy-ethane / 15 h / 23 °C 2: isopropylcyclohexylamine, methylmagnesium bromide / tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) 23 deg C, 3,5 h View Scheme

N-cyclohexyl-N-isopropylamine; methylmagnesium bromide in tetrahydrofuran 1.) 0 deg C, 0.5 h, 2.) 23 deg C, 3,5 h; Yield given. Yields of byproduct given;

1: 90 percent / H2, quinoline / Pd/BaSO4 2: 95 percent / PPh3, Br2 / 3 h / Ambient temperature 3: 1.) t-BuLi / 1.) THF, 2.) THF, -50 deg C, 1 h 4: bipyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 5: I2 / diethyl ether / 4 h / Ambient temperature 6: NaBH4 / methanol / 0.25 h / 0 °C 7: imidazole / dimethylformamide / 2.5 h / 50 °C 8: diisobutylaluminium hydride / CH2Cl2 / 0.08 h / -78 °C 9: pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 10: 83 percent / 48percent aq. HF / acetonitrile / 2 h / Ambient temperature 11: 85 percent / pyridine / 4 h / Ambient temperature 12: t-BuOK / tetrahydrofuran 13: 100 percent / LiOH / propan-2-ol; H2O View Scheme

1: oxalyl chloride, DMF / benzene / Ambient temperature 2: benzene; diethyl ether / -10 - -5 °C 3: Rh(OAc)2 / 1 h / Ambient temperature 4: CeCl3*5H2O, NaBH4 / propan-2-ol; H2O 5: pyridine / 0 °C 6: imidazole / dimethylformamide / Ambient temperature 7: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr 8: 46 percent / 80percent AcOH / 48 h / Ambient temperature 9: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature 10: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h 11: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr 12: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 13: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme