1: sodium borohydride / methanol / 2 h 2: H2SO4 / methanol / 48 h / 20 °C View Scheme

sulfuric acid

hydrogenchloride; formic acid; ethanol; nickel; zinc dibromide 1) CH2Cl2, RT, 3 min, 2) 5 min, reflux; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.0 g / LiBH4 / ethanol / 1.5 h / Ambient temperature 2: 17.5 mg / 4-pyrrolidinopyridine, DCC / diethyl ether / 5 h / 20 °C 3: 1.5 mg / 1N HCl / tetrahydrofuran / 18 h / 20 °C View Scheme

Multi-step reaction with 4 steps 1: 65 percent / AgNO3, NaOH / methanol2: 85 percent / HNEt2, DCC / CH2Cl2 3: 80 percent / H2 / Pd-C / methanol4: CF3COOH / H2O / 0 °C  

Multi-step reaction with 12 steps 1.1: triphenylphosphine / CH2Cl2 / 0.5 h / -20 °C1.2: 86 percent / triethylamine / CH2Cl2 / 0.5 h / 0 °C2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -78 °C2.2: 82 percent / tetrahydrofuran; hexane / 2.5 h / 20 °C3.1: 96 percent / carbon tetrachloride; triphenylphosphine; sodium bicarbonate / 4 h / Heating4.1: 85 percent / lithium amide / tetrahydrofuran; hexamethylphosphoric acid triamide; liquid ammonia / 0.5 h5.1: 88 percent / imidazole / CH2Cl2 / 24 h / 20 °C6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C6.2: BF3*OEt2 / tetrahydrofuran; hexane / 0.5 h / -78 °C6.3: 75 percent / tetrahydrofuran; hexane / 1 h / -78 °C7.1: 91 percent / imidazole / CH2Cl2 / 6 h / 20 °C8.1: 94 percent / CuCl2*2H2O / acetonitrile / 3 h / 20 °C9.1: 89 percent / triphenylphosphine; I2; imidazole / toluene / 3 h / Heating10.1: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1 h / 20 °C11.1: 81 percent / 4-dimethylaminopyridine; triethylamine / CH2Cl2 / 48 h / 20 °C12.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C