1: With diisobutylaluminium hydride in dichloromethane; toluene T=-78 - 20°C; 2.16667 h; 2: With water; acetic acid in dichloromethane; toluene T=0°C;

1: 1-iodo-5-methoxynaphthalene With n-butyllithium in tetrahydrofuran; cyclohexane T=-78°C; 0.25 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; cyclohexane T=-78°C; 0.25 h; Further stages.;

hydrogenchloride in tetrahydrofuran 2 h;

1: 98 percent / toluene-p-sulphonic acid / tetrahydrofuran / 0.25 h / 0 °C 2: 1) butyllithium, 2) 1,2-dibromoethane / 1) hexane, THF, r.t., 3 h, 2) r.t., 1 h 3: dil. HCl / 0.5 h / Ambient temperature 4: 92 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 5: 169 mg / 1) butyllithium, 2) ennecarbonyldiiron / 1) THF, hexane, -100 deg C, 30 min., 2) benzene, reflux, 20 h 6: 94 percent / conc. HCl / tetrahydrofuran / 2 h View Scheme

1: 1) butyllithium, 2) 1,2-dibromoethane / 1) hexane, THF, r.t., 3 h, 2) r.t., 1 h 2: dil. HCl / 0.5 h / Ambient temperature 3: 92 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 4: 169 mg / 1) butyllithium, 2) ennecarbonyldiiron / 1) THF, hexane, -100 deg C, 30 min., 2) benzene, reflux, 20 h 5: 94 percent / conc. HCl / tetrahydrofuran / 2 h View Scheme

1: 169 mg / 1) butyllithium, 2) ennecarbonyldiiron / 1) THF, hexane, -100 deg C, 30 min., 2) benzene, reflux, 20 h 2: 94 percent / conc. HCl / tetrahydrofuran / 2 h View Scheme

1: 92 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 2: 169 mg / 1) butyllithium, 2) ennecarbonyldiiron / 1) THF, hexane, -100 deg C, 30 min., 2) benzene, reflux, 20 h 3: 94 percent / conc. HCl / tetrahydrofuran / 2 h View Scheme