1: 60 percent / NaCl / dimethylsulfoxide; H2O / 8 h / 180 °C 2: 95 percent / H2 / Lindlar's catalyst / hexane 3: 70 percent / LiAlH4 / diethyl ether / 1) overnight, r.t., then 6 h, reflux. 4: 90 percent / PBr3, pyridine / diethyl ether / 1) overnight, r.t., then 2 h, reflux. 5: 1) Mg turnings / 1) THF, 2) THF, HMPA, 16 h, -10 deg C. 6: 80 percent / acetyl chloride, glacial acetic acid / 35 - 40 °C View Scheme

water; sodium hydroxide 2 h; RefluxInert atmosphere;

1: 60 percent / NaCl / dimethylsulfoxide; H2O / 8 h / 180 °C 2: 95 percent / H2 / Lindlar's catalyst / hexane 3: 70 percent / LiAlH4 / diethyl ether / 1) overnight, r.t., then 6 h, reflux. View Scheme