1: 1.) Mg, BrCH2CH2Br, I2 / 1.) Et2O, reflux, 1 h, 2.) 16 h 2: conc. HCl / ethanol / 2 h / Heating 3: 83 percent / CH3ONa / dimethylformamide / 2 h / 35 °C 4: 84 percent / 1.5M NaOH, Bu4NHSO4, 2,6-di-t-butyl-4-methylphenol / H2O / 3 h / Heating 5: 86 percent / methanol / 16 h / 65 °C View Scheme

1: 1.) Mg, BrCH2CH2Br, I2 / 1.) Et2O, reflux, 1 h, 2.) 16 h 2: conc. HCl / ethanol / 2 h / Heating 3: 83 percent / CH3ONa / dimethylformamide / 2 h / 35 °C 4: 1.) NaH / 1.) DMF, 2.) 50 deg C View Scheme

1: 1.) Mg, BrCH2CH2Br, I2 / 1.) Et2O, reflux, 1 h, 2.) 16 h 2: conc. HCl / ethanol / 2 h / Heating 3: 88 percent / CH3ONa / dimethylformamide / 2 h / 35 °C 4: 1.) NaH / 1.) DMF, 2.) 60 deg C, 30 min View Scheme

1: 1.) Mg, BrCH2CH2Br, I2 / 1.) Et2O, reflux, 1 h, 2.) 16 h 2: conc. HCl / ethanol / 2 h / Heating 3: 83 percent / CH3ONa / dimethylformamide / 2 h / 35 °C 4: 84 percent / 1.5M NaOH, Bu4NHSO4, 2,6-di-t-butyl-4-methylphenol / H2O / 3 h / Heating 5: 94 percent / dimethylformamide / 1.5 h / 80 °C View Scheme

1: 1.) Mg, BrCH2CH2Br, I2 / 1.) Et2O, reflux, 1 h, 2.) 16 h 2: conc. HCl / ethanol / 2 h / Heating 3: 1.) CH3ONa, 2.) 1.2M NaOH, Bu4NHSO4 / 1.) DMF, 35 deg C, 1 h, 2.) CH2Cl2, H2O, 10 min 4: 89 percent / NaOH / H2O; methanol / 0.08 h / Heating View Scheme