sodium tetrahydroborate in ethanol T=20°C; 5 h;

in N-methyl-acetamide; benzene-dimethylformamide

1: 71 percent / methanolic benzyltrimethylammonium hydroxide / dioxane / 24 h / Heating 2: 91 percent / sodium borohydride / ethanol / 1 h / 20 °C View Scheme

1: 64 percent / Jones chromic acid reagent / acetone / 0 °C 2: 71 percent / methanolic benzyltrimethylammonium hydroxide / dioxane / 24 h / Heating 3: 91 percent / sodium borohydride / ethanol / 1 h / 20 °C View Scheme

1: 96.5 g / magnesium / tetrahydrofuran / Ambient temperature 2: 64 percent / Jones chromic acid reagent / acetone / 0 °C 3: 71 percent / methanolic benzyltrimethylammonium hydroxide / dioxane / 24 h / Heating 4: 91 percent / sodium borohydride / ethanol / 1 h / 20 °C View Scheme