1: 1) NaH / 1) THF, below 20 deg C 2a) r.t., 6h 2b) 60 deg C, 3h 2: 60 percent / LiAlH4 / benzene / 1) r.t., 2h 2) 60 deg C, 12h 3: 94 percent / NEt3 / CH2Cl2 / 0.5 h / 0 °C 4: 40 percent / CuI / diethyl ether / 1) 0 deg C, 4 h 2) r.t. 5: 95 percent / conc.HCl / methanol / 4 h View Scheme

1: 78.8 percent / CH2Cl2 / 26 h 2: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature View Scheme

1: 78.8 percent / CH2Cl2 / 26 h 2: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature 3: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h View Scheme

1: 78.8 percent / CH2Cl2 / 26 h 2: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature 3: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h 4: 100 percent / PPTS / ethanol / 3 h / 70 °C View Scheme

1: 78.8 percent / CH2Cl2 / 26 h 2: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature 3: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h 4: AcOH 5: H2 View Scheme