acetic acid in water 1.5 h; Heating;

1: 90 percent / triethylamine / CH2Cl2 / 12 h 2: 1.) pyridinium p-toluenesulfonate, 2.) lithium borohydride / 1.) dichloromethane, room temperature 3 h, 2.) THF 3: 7.5 g / triethylamine / CH2Cl2 / 1 h / 0 °C 4: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating 5: 60 percent / acetic acid / H2O / 1.5 h / Heating View Scheme

1: 1.) pyridinium p-toluenesulfonate, 2.) lithium borohydride / 1.) dichloromethane, room temperature 3 h, 2.) THF 2: 7.5 g / triethylamine / CH2Cl2 / 1 h / 0 °C 3: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating 4: 60 percent / acetic acid / H2O / 1.5 h / Heating View Scheme

1: 90 percent / triethylamine / CH2Cl2 / 12 h 2: 1.) pyridinium p-toluenesulfonate, 2.) lithium borohydride / 1.) dichloromethane, room temperature 3 h, 2.) THF 3: 7.5 g / triethylamine / CH2Cl2 / 1 h / 0 °C 4: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating 5: 60 percent / acetic acid / H2O / 1.5 h / Heating View Scheme

1: 7.5 g / triethylamine / CH2Cl2 / 1 h / 0 °C 2: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating 3: 60 percent / acetic acid / H2O / 1.5 h / Heating View Scheme

1: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating 2: 60 percent / acetic acid / H2O / 1.5 h / Heating View Scheme

1: acetyl chloride / 8 h / Heating 2: 90 percent / triethylamine / CH2Cl2 / 12 h 3: 1.) pyridinium p-toluenesulfonate, 2.) lithium borohydride / 1.) dichloromethane, room temperature 3 h, 2.) THF 4: 7.5 g / triethylamine / CH2Cl2 / 1 h / 0 °C 5: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating 6: 60 percent / acetic acid / H2O / 1.5 h / Heating View Scheme