1: 97 percent / oxalyl chloride / CH2Cl2 / Ambient temperature 2: 92 percent / FeCl3 / CH2Cl2 / -20 °C 3: 62.4 percent / NaH / 1,2-dimethoxy-ethane / 1.) from -10 deg C to RT, 15 min, 2.) reflux, 1 h 4: 1.) n-BuLi, 2.) Me3SnCl, 3.) Pd(PPh3)4, LiCl 5: 96.1 percent / Bu4NF / tetrahydrofuran / 0.08 h / 0 °C 6: 98.7 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -78 °C 7: LiN(TMS)2 / tetrahydrofuran / 5 h / Ambient temperature 8: oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -78 °C 9: 1.) H2, 2.) KI, acetic acid / 1.) 5percent Pd/BaSO4 / 1.) pyridine, RT, 8 min, 2.) RT, 30 min View Scheme

palladium dichloride

1) alkylation; 2) pyridine, heating; Yield given. Multistep reaction;

sodium hydroxide Heating;

lithium aluminium tetrahydride in diethyl ether T=0°C; 2 h;

1: 93.5 percent / LiAlH4 / diethyl ether / 2 h / 0 °C 2: 1.) n-BuLi / 1.) THF, -42 deg C, 2 h, 2.) 0.5 h 3: 0.4 M CrSO4 / H2O / 12 h / Ambient temperature 4: 90.6 percent / concd H2SO4 / 50 h / Ambient temperature 5: 93 percent / pyridinium chlorochromate / CH2Cl2 / 3.5 h / Ambient temperature View Scheme