1: 30.1 percent / K2CO3 / dimethylsulfoxide / 30 h / Ambient temperature 2: ethyl acetate; diisopropyl ether 3: 96 percent / H2 / Pd / ethanol / 3 h / 760 Torr / Ambient temperature View Scheme

1: 30.1 percent / K2CO3 / dimethylsulfoxide / 30 h / Ambient temperature 2: ethyl acetate; diisopropyl ether 3: 96 percent / H2 / Pd / ethanol / 3 h / 760 Torr / Ambient temperature 4: DCC / tetrahydrofuran / Ambient temperature 5: 1) tBuOK / 1) THF, -50 deg C, 20 min, 2) THF, -30 deg C, 20 min 6: ethyl acetate; diisopropyl ether / 3 h / Ambient temperature 7: 1) K2CO3, 2) 15percent HCl/dioxane / 1) H2O, 2) rt, overnight View Scheme

triethylamine in N-methyl-acetamide; ethyl acetate

aluminum oxide; sodium carbonate; copper(ll) bromide in benzene T=50°C; 1.5 h;

1: With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: With 1,2-dibromo-1,1,2,2-tetrafluoroethane in tetrahydrofuran; hexane T=-78°C; 0.5 h;

LiCO3 in tetrahydrofuran 1.5 h; Heating;

1: 72.8 percent / sodium ethylate / 4 h / Heating 2: 1.) 50percent NaH; 2.) bromine, Ba(OH)2 / 1.) mineral oil, THF, 30 min; 2.) CH2Cl2, EtOH, 0 degC, 30 min View Scheme

sulfuric acid