1: 1.) potassium hexamethyldisilazide (KHMDS) / 1.) THF, toluene, -78 deg C, 1 h, 2.) THF, toluene, 3 h 2: 24 percent / LiAlH4 / tetrahydrofuran / 4 h / -78 °C 3: 88 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 4: 90 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme

sodium hydroxide; sulfuric acid 1) 0 deg C, 40 h irradiation (2500-3000 Angstroem); 2) 0 deg C, pH 7-7.4, then 2 h reflux in 0.24N methanolic NaOH; further activation methods; Yield given. Multistep reaction;

1: 70 percent / thionyl chloride / 10 h / Heating 2: 90 percent / NaOCl / CH2Cl2; H2O / 0.83 h / 0 - 5 °C / further reagent; further solvent 3: 38 percent / 1) 85percent H2SO4; 2) 2N NaOH / 1) 0 deg C, 40 h irradiation (2500-3000 Angstroem); 2) 0 deg C, pH 7-7.4, then 2 h reflux in 0.24N methanolic NaOH; further activation methods View Scheme

1: 90 percent / NaOCl / CH2Cl2; H2O / 0.83 h / 0 - 5 °C / further reagent; further solvent 2: 38 percent / 1) 85percent H2SO4; 2) 2N NaOH / 1) 0 deg C, 40 h irradiation (2500-3000 Angstroem); 2) 0 deg C, pH 7-7.4, then 2 h reflux in 0.24N methanolic NaOH; further activation methods View Scheme

hydrogenchloride T=120°C; 48 h; Further byproducts given;

hydrogenchloride T=120°C; 48 h; Further byproducts given;

Yield given. Multistep reaction;