Yield given. Multistep reaction;

1: 1) n-BuLi, 2) glacial acetic acid, 10percent aq. HCl / 1a) ether/hexane, -60 deg C, 1 h, 1b) RT, overnight 2: pyridinium p-toluenesulfonate / benzene / 120 h / Heating 3: 1) B2H6, 2) 3N NaOH, 30 percent H2O2 / 1) THF, RT, overnight, 2a) 45 deg C, 5 h, 2b) RT 4: sodium acetate, pyridinium chlorochromate / CH2Cl2 View Scheme

sodium acetate; pyridinium chlorochromate in dichloromethane Yield given;

1: pyridinium p-toluenesulfonate / benzene / 120 h / Heating 2: 1) B2H6, 2) 3N NaOH, 30 percent H2O2 / 1) THF, RT, overnight, 2a) 45 deg C, 5 h, 2b) RT 3: sodium acetate, pyridinium chlorochromate / CH2Cl2 View Scheme

1: 1) n-BuLi, 2) glacial acetic acid, 10percent aq. HCl / 1a) ether/hexane, -60 deg C, 1 h, 1b) RT, overnight 2: pyridinium p-toluenesulfonate / benzene / 120 h / Heating 3: 1) B2H6, 2) 3N NaOH, 30 percent H2O2 / 1) THF, RT, overnight, 2a) 45 deg C, 5 h, 2b) RT 4: sodium acetate, pyridinium chlorochromate / CH2Cl2 View Scheme

View Scheme