1: With n-butyllithium in hexane; toluene T=0 - 5°C; Inert atmosphere; 2: With diisobutylaluminium hydride in hexane; toluene T=0 - 50°C; Inert atmosphere;

in acetic acid 15 h; Ambient temperature;

in dichloromethane

Verb.5: Essigsaeure;

1: dimethyl sulfate; acetic acid; THF / Erwaermen des Reaktionsprodukts in H2O mit KCN 2: Raney nickel; NH3; methanol / 73550.8 Torr / Hydrogenation View Scheme

1: benzene 2: 82.9 percent / aq. ethanol / 24 h / Heating 3: 98.1 percent / KOH / aq. ethanol / 36 h / Heating View Scheme

ethanol; dimethyl sulfate Erwaermen des Reaktionsprodukts mit wss. NaOH;

1: 97 percent / NaH / tetrahydrofuran / 0 °C 2: 1.) t-BuLi, 2.) Cl3CCCl3 / 1.) ether, pentane, -78 deg C, 20 min, 0 deg C, 1 h, 2.) ether, pentane, -78 deg C to rt 3: benzene / Ambient temperature 4: 3.46 g / TBAF / tetrahydrofuran / 1 h 5: 99 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C 6: 52 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature; other solvent, reagent, temperature, reaction time 7: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time 8: O2, salcomine / dimethylformamide / 2 h / Ambient temperature 9: methanol / 23 h / Ambient temperature View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran; dichloromethane; ethyl acetate; toluene

in dimethyl sulfoxide; ethyl acetate T=80°C;