sodium hydroxide in DMF (N,N-dimethyl-formamide) T=0 - 20°C;

toluene; benzyl alcohol

cerium(III) chloride in methanol Ambient temperature;

[2,2']bipyridinyl; copper(l) chloride in 1,2-dichloro-ethane 3 h; Inert atmosphereReflux;

diethyl ether; ammonia; sodium

1: 90 percent / BF3*OEt2 / CH2Cl2 / 0 °C 2: 95 percent / LiAlH4 / diethyl ether / 0 deg C to RT 3: 90 percent / Heating 4: 81 percent / POCl3, Et3N / tetrahydrofuran / 0 °C 5: 81 percent / LDA / tetrahydrofuran / -78 °C 6: 96 percent / LDA / tetrahydrofuran / 1 h / -78 °C 7: 91 percent / conc. aq. HCl / tetrahydrofuran / 0.17 h / 0 °C View Scheme

2,4-dinitrobenzenesulfonic acid in acetonitrile T=20°C; Hosomi-Sakurai reaction; 7 h;