n-butyllithium in tetrahydrofuran; hexane T=0 - 20°C; Wittig reaction; 14 h;

1: 72 percent / n-BuLi; i-Pr2NH / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C 2: 97 percent / n-BuLi / tetrahydrofuran; hexane / 14 h / 0 - 20 °C View Scheme

1: 1.03 g / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 2: 80 percent / N,N'-dicyclohexylcarbodiimide; H3PO4; DMSO / 1.5 h / 20 °C 3: 97 percent / n-BuLi / tetrahydrofuran; hexane / 14 h / 0 - 20 °C View Scheme

1: 98 percent / KMnO4; H2O / 20 h / Heating 2: Et3N / benzene / 1 h / 20 °C 3: 1.03 g / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 4: 80 percent / N,N'-dicyclohexylcarbodiimide; H3PO4; DMSO / 1.5 h / 20 °C 5: 97 percent / n-BuLi / tetrahydrofuran; hexane / 14 h / 0 - 20 °C View Scheme

1: Et3N / benzene / 1 h / 20 °C 2: 1.03 g / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 3: 80 percent / N,N'-dicyclohexylcarbodiimide; H3PO4; DMSO / 1.5 h / 20 °C 4: 97 percent / n-BuLi / tetrahydrofuran; hexane / 14 h / 0 - 20 °C View Scheme

1: 80 percent / N,N'-dicyclohexylcarbodiimide; H3PO4; DMSO / 1.5 h / 20 °C 2: 97 percent / n-BuLi / tetrahydrofuran; hexane / 14 h / 0 - 20 °C View Scheme