1: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 2: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 3: 5percent aq. NaOH / methanol / 4 h / 20 °C 4: 85.5 percent / H2 / Pd/CaCO3/Pb View Scheme

1: PBr3, Py / diethyl ether 2: (i) EtMgBr, THF, Et2O, (ii) /BRN= 1817367/, CuCl 3: H2 / Lindlar catalyst / 0 °C / 760 Torr View Scheme