1: 94 percent / p-TsOH*H2O / benzene / 3 h / Heating 2: 69 percent / NaBH3CN, glacial AcOH / 0.5 h / 28 °C 3: 92 percent / POCl3, pyridine / 0.5 h / 80 - 90 °C 4: 74 percent / Raney Ni / ethanol / 1 h View Scheme

1: 1.) p-toluenesulfonic acid monohydrate, 2.) NaBH4 / 1.) C6H6, reflux, 2.) MeOH, RT, 1 h 2: 96 percent / 6N aq. HCl / methanol / 2 h / Heating View Scheme

sodium tetrahydroborate in ethanol 6 h;

1: 1.) p-toluenesulfonic acid monohydrate, 2.) NaBH4 / 1.) C6H6, reflux, 2.) MeOH, RT, 1 h 2: 96 percent / 6N aq. HCl / methanol / 2 h / Heating View Scheme