super deuteride; p-toluenesulfonyl chloride 1.) pyridine, -5 deg C, 24 h, 2.) THF; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

super deuteride; p-toluenesulfonyl chloride 1.) pyridine, -5 deg C, 24 h, 2.) THF; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

super deuteride; p-toluenesulfonyl chloride 1.) pyridine, -5 deg C, 24 h, 2.) THF; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

1: pyridinium chlorochromate, Celite 545 / CH2Cl2 / 24 h / Ambient temperature 2: NaBH4 / ethanol / 4 h / Ambient temperature 3: 71 percent / HgO, I2 / benzene / 2 h / Ambient temperature; Irradiation 4: NaCNBH3 / hexamethylphosphoric acid triamide / Ambient temperature View Scheme

1: pyridinium chlorochromate, Celite 545 / CH2Cl2 / 24 h / Ambient temperature 2: NaBH4 / ethanol / 4 h / Ambient temperature 3: 71 percent / HgO, I2 / benzene / 2 h / Ambient temperature; Irradiation 4: 61 percent / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: pyridinium chlorochromate, Celite 545 / CH2Cl2 / 24 h / Ambient temperature 2: NaBH4 / ethanol / 4 h / Ambient temperature 3: 71 percent / HgO, I2 / benzene / 2 h / Ambient temperature; Irradiation View Scheme