chromium dichloride in acetone T=20°C; 0.5 h;

1: 85 percent / zinc / dimethylformamide / 0.5 h 2: 82 percent / aq. HCl / acetone / 1 h / Heating 3: 92 percent / diisopropylethylamine / 1,2-dichloro-ethane / 3 h / 55 °C 4: 91 percent / NaBH4 / ethanol / 0.5 h / 0 °C 5: 84 percent / imidazole / dimethylformamide / 1 h / 0 °C 6: 92 percent / OsO4; NaIO4 / tetrahydrofuran; H2O 7: 64 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 8: 74 percent / CrO3; H2SO4 / H2O / 0.5 h / 0 °C View Scheme

sodium methylate in methanol 1 h;

1: 69 percent / Zn / dimethylformamide / 0.5 h 2: 85 percent / aq. HCl / acetone / 1 h / Heating 3: 35 percent / Zn; NH4Cl / methanol / 2 h / Heating View Scheme

zinc in N,N-dimethyl-formamide Reformatsky reaction; 0.5 h;

1: 87 percent / Zn / dimethylformamide / 0.5 h 2: 84 percent / aq. HCl / acetone / 1 h / Heating View Scheme