N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium in tetrahydrofuran; diethyl ether T=-70°C;

1: 91 percent / imidazole / dimethylformamide / 0.5 h / Ambient temperature 2: 1.) n-BuLi, hexamethylphosphoramide (HMPA), triphenylmethane / 1.) ether, THF, -40 deg C, 15 min, 2.) RT, 30 h View Scheme

1: 100 percent / NaBH4, H2 / Ni(OAc)2 / ethanol 2: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 3: 95 percent / acetonitrile / 15 h / 85 °C 4: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 5: 70 percent / Bu4NF / tetrahydrofuran 6: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT 7: 92 percent / acetonitrile / 15 h / 85 °C 8: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 9: 92 percent / LiOH / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 100 percent / NaBH4, H2 / Ni(OAc)2 / ethanol 2: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 3: 95 percent / acetonitrile / 15 h / 85 °C 4: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 5: 70 percent / Bu4NF / tetrahydrofuran 6: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT 7: 92 percent / acetonitrile / 15 h / 85 °C 8: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT View Scheme

1: 100 percent / NaBH4, H2 / Ni(OAc)2 / ethanol 2: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 3: 95 percent / acetonitrile / 15 h / 85 °C 4: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 5: 70 percent / Bu4NF / tetrahydrofuran 6: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT View Scheme

1: 100 percent / NaBH4, H2 / Ni(OAc)2 / ethanol 2: 94 percent / PPh3, CBr4 / CH2Cl2 / 0 deg C to RT 3: 95 percent / acetonitrile / 15 h / 85 °C 4: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 5: 70 percent / Bu4NF / tetrahydrofuran View Scheme