thionyl chloride 16 h; Ambient temperature;

1: 1.) lithium amide / 1.) THF, 2 h, 2.) THF, 6 h 2: 83 percent / BF3*MeOH / 0.17 h / Heating View Scheme

1: 86 percent / HBr / 1 h / 100 - 110 °C 2: 1.) LiNH2 / 1.) liq. NH3, from -50 deg C to -40 deg C, 0.5 h, 2.) THF, liq. NH3, a) -33 deg C, 1 h, b) RT, 4 h 3: NaI / dimethylsulfoxide / 1.5 h / 100 - 125 °C 4: 10percent aq. NaOH / 5 h / 90 - 100 °C View Scheme

1: 89 percent / LiAlH4 / tetrahydrofuran / 2 h / -10 - 15 °C 2: 86 percent / HBr / 1 h / 100 - 110 °C 3: 1.) LiNH2 / 1.) liq. NH3, from -50 deg C to -40 deg C, 0.5 h, 2.) THF, liq. NH3, a) -33 deg C, 1 h, b) RT, 4 h 4: NaI / dimethylsulfoxide / 1.5 h / 100 - 125 °C 5: 10percent aq. NaOH / 5 h / 90 - 100 °C View Scheme

1: 91 percent / BuLi, LiBr / tetrahydrofuran; hexane / 1.) 0 deg C, 15 min, 2.) r.t., 30 min; reflux, 2 h 2: 99 percent / pyridine / 3 h / Ambient temperature 3: 1.) Jones reagent, 2.) AcCl / 1.) acetone, 0 deg C, 2.) r.t., 2 h View Scheme

copper(I) oxide; ethanol; calcium carbonate Reagens 4:Wasser, und Erwaermen des nach dem Ansaeuern erhaltenen Reaktionsprodukts mit Methanol, Benzol und wenig Schwefelsaeure;

1: 99 percent / pyridine / 3 h / Ambient temperature 2: 1.) Jones reagent, 2.) AcCl / 1.) acetone, 0 deg C, 2.) r.t., 2 h View Scheme

jones reagent; acetyl chloride 1.) acetone, 0 deg C, 2.) r.t., 2 h; Yield given. Multistep reaction;

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