1: 85 percent / KOH / ethanol / 2 h / Ambient temperature 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 20 min View Scheme

1: 85 percent / KOH / ethanol / 2 h / Ambient temperature 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 20 min 3: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 1.) -70 deg C, 20 min, 2.) -70 deg C, 2 h; -50 deg C, 30 min 4: KH / tetrahydrofuran / 1.) r.t., 20 min, 2.) r.t., 20 min 5: toluene / 2 h / Heating 6: H2 / PtO2 / ethyl acetate / 1 h / 2068.6 Torr 7: HCl / ethyl acetate / 1 h / 0 °C View Scheme