sulfuric acid; water; silica gel in toluene 0.5 h;

1: peroxyacetic acid; sodium acetate 2: tetrahydrofuran 3: acetic acid; aqueous methanol.H2SO4 4: ethanolic NaOH View Scheme

1: peroxyacetic acid; sodium acetate 2: tetrahydrofuran 3: acetic acid; aqueous methanol.H2SO4 4: HCl View Scheme

1: (n-Pr4N)(RuO4), 4-methylmorpholine N-oxide, molecular sieves / CH2Cl2 / Ambient temperature 2: 1.) t-BuLi / 1.) diethyl ether, pentane, -78 deg C, 1 h, 2.) diethyl ether, pentane, THF, -78 deg C, 11 h 3: 21 percent / Jones' reagent / acetone / 0.67 h / 0 °C 4: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / toluene / 5 h / 100 °C View Scheme