tetrabutyl ammonium fluoride in tetrahydrofuran

hydrogenchloride; mercury dichloride; zinc in water; toluene 48 h; Heating;

1: 1) n-BuLi / 1) THF, -78 deg C, 2 h, 2) -78 deg C, 30 min, then RT, 1 h. 2: 1) n-BuLi / 1) THF, 0 deg C, 1.3 h, 2) 0 deg C, 30 min, then RT, 90 min 3: 1) n-BuLi / 1) THF, 0 deg C, 2 h, 2) 0 deg C, 30 min, then RT, 2 h. 4: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1) n-BuLi / 1) THF, 0 deg C, 2 h, 2) 0 deg C, 30 min, then RT, 2 h. 2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1) n-BuLi / 1) THF, 0 deg C, 1.3 h, 2) 0 deg C, 30 min, then RT, 90 min 2: 1) n-BuLi / 1) THF, 0 deg C, 2 h, 2) 0 deg C, 30 min, then RT, 2 h. 3: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1) Li, 2) aq. HCl / 1) ethanol, 2-methyl-2-propanol, heating 14 h 2: 44 percent / Zn, HgCl2, conc. HCl / toluene; H2O / 48 h / Heating View Scheme

hydrogenchloride; aluminium trichloride