1: 92 percent / acetonitrile / 15 h / 85 °C 2: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 3: 92 percent / LiOH / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 92 percent / acetonitrile / 15 h / 85 °C 2: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT View Scheme

pyridine; PPh3.Br2 in acetonitrile 1 h; Ambient temperature;

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: DBU, CuI, HMPT / tetrahydrofuran 2: H2, (C2H5)N / Lindlar catalyst / tetrahydrofuran 3: CBr4, P(C6H5)3 / CH2Cl2 / 0.17 h / 0 °C View Scheme

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

1: 95 percent / acetonitrile / 15 h / 85 °C 2: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 3: 70 percent / Bu4NF / tetrahydrofuran 4: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT View Scheme

1: 70 percent / Bu4NF / tetrahydrofuran 2: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT View Scheme

1: 65 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 2: 70 percent / Bu4NF / tetrahydrofuran 3: 96 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT View Scheme