1.1: NaI / acetone / 20 °C 2.1: NaI; HOAc / acetone / Heating 3.1: 1.40 g / semicarbazide*HCl / H2O; acetic acid / 9.7 h / 80 - 85 °C 4.1: 1.42 g / DMAP; pyridine / 25 h 5.1: LiN(TMS)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -65 - -60 °C 5.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.03 h / -65 - 10 °C 6.1: 85.5 percent / CuCN / various solvent(s); tetrahydrofuran / 0.22 h / -45 °C 7.1: 63 percent / 4A molecular sieves; benzyltrimethylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C 8.1: 97 percent / aq. HCl / methanol / 2.5 h / 0 - 20 °C View Scheme

1: NaI / acetone / 20 °C 2: NaI; HOAc / acetone / Heating View Scheme