n-butyllithium in tetrahydrofuran T=-78°C; 30 h;

1: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 2: 4.34 g / CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 3: 87 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C View Scheme

1: With 2,6-dimethylpyridine; triphenylphosphine in dichloromethane T=0°C; Corey-Fuchs homologation; 1.5 h; Inert atmosphere; 2: With n-butyllithium in tetrahydrofuran T=-40°C; Corey-Fuchs homologation; 0.666667 h; Inert atmosphere; 3: With water; ammonium chloride in tetrahydrofuran Inert atmosphere;

1: 94 percent / L-(+)-diethyl tartarate, Ti(OPr-i)4, t-BuOOH, molecular sieves 4A / CH2Cl2 / 20 h / -20 °C 2: 77 percent / hexane; CH2Cl2 / 16 h / 0 - 20 °C 3: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 4: PPh3 / CH2Cl2 / 0.33 h / 0 °C 5: 87 percent / BuLi / tetrahydrofuran / 30 h / -78 °C View Scheme

1: 77 percent / hexane; CH2Cl2 / 16 h / 0 - 20 °C 2: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 3: PPh3 / CH2Cl2 / 0.33 h / 0 °C 4: 87 percent / BuLi / tetrahydrofuran / 30 h / -78 °C View Scheme

1: 80 percent / benzene / 15 h / Ambient temperature 2: 1) Ti(Oi-Pr)4, diethyl L-(+)-tartrate, tert-butyl hydroperoxide, 4 Angstroem molecular sieves / 1) CH2Cl2, -20 deg C, 20 h, 2) CH2Cl2, hexane, room temperature, 16 h 3: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 4: 4.34 g / CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 5: 87 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C View Scheme

1: 69 percent / NaH / tetrahydrofuran; dimethylformamide / 18 h / Ambient temperature 2: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, 0 deg C, 10 min; room temperature, 30 min 3: 80 percent / benzene / 15 h / Ambient temperature 4: 1) Ti(Oi-Pr)4, diethyl L-(+)-tartrate, tert-butyl hydroperoxide, 4 Angstroem molecular sieves / 1) CH2Cl2, -20 deg C, 20 h, 2) CH2Cl2, hexane, room temperature, 16 h 5: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 6: 4.34 g / CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 7: 87 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C View Scheme

1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, 0 deg C, 10 min; room temperature, 30 min 2: 80 percent / benzene / 15 h / Ambient temperature 3: 1) Ti(Oi-Pr)4, diethyl L-(+)-tartrate, tert-butyl hydroperoxide, 4 Angstroem molecular sieves / 1) CH2Cl2, -20 deg C, 20 h, 2) CH2Cl2, hexane, room temperature, 16 h 4: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 5: 4.34 g / CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 6: 87 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C View Scheme

1: 1) Ti(Oi-Pr)4, diethyl L-(+)-tartrate, tert-butyl hydroperoxide, 4 Angstroem molecular sieves / 1) CH2Cl2, -20 deg C, 20 h, 2) CH2Cl2, hexane, room temperature, 16 h 2: NaIO4 / tetrahydrofuran; H2O / 0.17 h / Ambient temperature 3: 4.34 g / CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 4: 87 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C View Scheme

1: PPh3 / CH2Cl2 / 0.33 h / 0 °C 2: 87 percent / BuLi / tetrahydrofuran / 30 h / -78 °C View Scheme