in tetrahydrofuran; hexane T=0 - 20°C; 2 h;

1: 1.) NaNH2 / 1.) ether, 15 min, 0 deg C; 2.) ether-DMSO, RT, 1 h 2: Zn, KCN / methanol; H2O / 24 h / Ambient temperature View Scheme

copper(l) chloride; zinc in ethanol Heating;

triphenylphosphine in diethyl ether 0.25 h; Ambient temperature;

1: 70 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1.5 h 2: 1.) sodium bis(trimethylsilyl)amide / 1.) n-hexane, reflux, 3 h, 2.) THF, -78 deg C, 1.5 h; warm to ambient temperature View Scheme

1: 72 percent / LiAlH4 / diethyl ether / Heating 2: 70 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1.5 h 3: 1.) sodium bis(trimethylsilyl)amide / 1.) n-hexane, reflux, 3 h, 2.) THF, -78 deg C, 1.5 h; warm to ambient temperature View Scheme

potassium cyanide; zinc in methanol; water 24 h; Ambient temperature; Yield given. Yields of byproduct given;

1: 91 percent / MnO2 / CH2Cl2 / 1.5 h 2: 33 percent / tetrahydrofuran / 1 h / 0 °C 3: Zn(Cu,Ag) / H2O; methanol / Ambient temperature View Scheme

sodium hexamethyldisilazane 1.) n-hexane, reflux, 3 h, 2.) THF, -78 deg C, 1.5 h; warm to ambient temperature; Yield given. Multistep reaction;

1: 1.) NaH / 1.) THF, 30 min, 2.) THF, 2 h 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2 h, 2.) 2.) CH2Cl2, from -78 deg C to RT, 75 min 3: 78 percent / LiBH4 / tetrahydrofuran / 0.5 h / 20 °C 4: 86 percent / LiCl, MsCl, s-collidine / dimethylformamide / 2 h / 0 - 20 °C 5: 79 percent / tetrahydrofuran / 12 h / Ambient temperature 6: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 7: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h 8: 85 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme