hydrogenchloride; zinc(II) chloride

hydrogenchloride

(i) aq. HIO4, (ii) /BRN= 773638/, HCl, Ba(OAc)2; Multistep reaction;

1: pyridinium p-toluenesylfonate / acetone 2: NaH / tetrahydrofuran / 0 °C 3: HgO, BF3*Et2O / tetrahydrofuran; H2O / 0.5 h 4: 7.0 g / diethyl ether / 2 h / 0 °C 5: 86 percent / AcOH / H2O / 16 h 6: H2SO4 / tetrahydrofuran / 50 °C 7: 81 percent / KBr, AcO2H, NaOAc / acetic acid / 2 h / 10 °C 8: 77 percent / H2 / Pd/C / methanol View Scheme

1: pyridinium p-toluenesylfonate / acetone 2: NaH / tetrahydrofuran / 0 °C 3: HgO, BF3*Et2O / tetrahydrofuran; H2O / 0.5 h 4: 7.0 g / diethyl ether / 2 h / 0 °C 5: 86 percent / AcOH / H2O / 16 h 6: H2SO4 / tetrahydrofuran / 50 °C 7: 81 percent / KBr, AcO2H, NaOAc / acetic acid / 2 h / 10 °C 8: 95 percent / H2 / Pd/C / methanol View Scheme

ethanol; nickel

1: pyridinium p-toluenesylfonate / acetone 2: NaH / tetrahydrofuran / 0 °C 3: HgO, BF3*Et2O / tetrahydrofuran; H2O / 0.5 h 4: 7.0 g / diethyl ether / 2 h / 0 °C 5: 86 percent / AcOH / H2O / 16 h 6: H2SO4 / tetrahydrofuran / 50 °C 7: 81 percent / KBr, AcO2H, NaOAc / acetic acid / 2 h / 10 °C View Scheme

1: 1.) HgO, HgCl2 2.) pyridine / 1.) -20 deg C --> r.t., 5 h; 2.) -20 deg C 2: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / Heating View Scheme

4-(N,N-dimethlyamino)pyridine in pyridine T=70°C;

pyridine