1.1: NaH; n-BuLi / tetrahydrofuran 1.2: tetrahydrofuran 2.1: aq. NaOH / tetrahydrofuran / 20 - 60 °C View Scheme

sodium in ethanol

1.1: N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: Pd(1,3-bis(diphenylphosphino)-propane)Cl2; lithium triethylborohydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere View Scheme

ammonia in methanol 16 h;

1: 70 percent / zinc acetate; TFA / dimethylformamide; acetonitrile; H2O / 24 h 2: 84 percent / LiOH / methanol; H2O / 24 h View Scheme

zinc diacetate; trifluoroacetic acid in water; N,N-dimethyl-formamide; acetonitrile 24 h;

1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere; |Cooling with acetone-dry ice 4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / |Inert atmosphere; |Cooling with acetone-dry ice 5.1: Pd(1,2-bis(diphenylphosphino)ethane)Cl2 / tetrahydrofuran / 0.08 h / 0 °C / |Cooling with acetone-dry ice; |Inert atmosphere 5.2: 4.5 h / 0 °C / |Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme

1: 1) tetrabutylammonium chloride, NaOH / 1) benzene, H2O, room temperature, 20 min, 2) benzene, room temperature, 2 days 2: 66 percent / K2CO3 / o-xylene / 13 h / Heating View Scheme

das beim Behandeln mit 4-Nitroso-dimethylanilin in waessrig-alkoholischer NaOH bei Zimmertemperatur und folgenden Zerlegen mit Wasser;

2: 30percent H2O2, KHCO3, KF 3: 20 percent / PDC View Scheme