1: 90 percent / Jones reagent / acetone / 0.25 h / 0 °C 2: 91 percent / zinc dust, AcOH / CHCl3 / 2 h / Ambient temperature View Scheme

1: 78 percent / Ag2O / acetone / 24 h / 20 °C 2: 90 percent / LiAlH4 / diethyl ether / 0.5 h / -60 °C 3: 72 percent / NBS; Me2S / CH2Cl2 / 1 h 4: 90 percent / Jones reagent / acetone / 0.5 h 5: 68 percent / Et3N / 0.5 h / Heating View Scheme