1: CH2Cl2 / 14 h / Ambient temperature 2: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 3: 1.) CuI, 2.) n-butyllithium, 4.) MeOH / 1.) diethyl ether, -78 deg C, 0.5 h, 2.) diethyl ether, room temperature, 40 min, 3.) diethyl ether, room temperature, 16 h 4: 1.) 4.5 N HCl / 1.) reflux View Scheme

1: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 2: 1.) CuI, 2.) n-butyllithium, 4.) MeOH / 1.) diethyl ether, -78 deg C, 0.5 h, 2.) diethyl ether, room temperature, 40 min, 3.) diethyl ether, room temperature, 16 h 3: 1.) 4.5 N HCl / 1.) reflux View Scheme

1: thionyl chloride / 1 h / 100 °C 2: CH2Cl2 / 14 h / Ambient temperature 3: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 4: 1.) CuI, 2.) n-butyllithium, 4.) MeOH / 1.) diethyl ether, -78 deg C, 0.5 h, 2.) diethyl ether, room temperature, 40 min, 3.) diethyl ether, room temperature, 16 h 5: 1.) 4.5 N HCl / 1.) reflux View Scheme

1: 93 percent / 2,6-lutidine 2: 97 percent / H2 / Pd/C 3: 77 percent / TBAF / tetrahydrofuran 4: 1.) SO2Cl2, 2.) MeOH 5: 75 percent / TFA / CH2Cl2 6: 1.) MsCl, Et3N, 2.) DBU / 2.) THF View Scheme

1: 97 percent / H2 / Pd/C 2: 77 percent / TBAF / tetrahydrofuran 3: 1.) SO2Cl2, 2.) MeOH 4: 75 percent / TFA / CH2Cl2 5: 1.) MsCl, Et3N, 2.) DBU / 2.) THF View Scheme

1: 81 percent / n-BuLi / tetrahydrofuran 2: 93 percent / 2,6-lutidine 3: 97 percent / H2 / Pd/C 4: 77 percent / TBAF / tetrahydrofuran 5: 1.) SO2Cl2, 2.) MeOH 6: 75 percent / TFA / CH2Cl2 7: 1.) MsCl, Et3N, 2.) DBU / 2.) THF View Scheme

1: 1.) CuI, 2.) n-butyllithium, 4.) MeOH / 1.) diethyl ether, -78 deg C, 0.5 h, 2.) diethyl ether, room temperature, 40 min, 3.) diethyl ether, room temperature, 16 h 2: 1.) 4.5 N HCl / 1.) reflux View Scheme

hydrogenchloride 1.) reflux; Yield given. Multistep reaction;

1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / benzene / 80 °C / |Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / ethanol View Scheme