pyridine T=220°C; 72 h;

sodium hydroxide in pentan-1-ol T=170°C; 72 h;

1: 100 percent / NaOH / pentan-1-ol / 72 h / 170 °C 2: LiAlH4 / diethyl ether View Scheme

1.1: 100 percent / NaOH / pentan-1-ol / 72 h / 170 °C 2.1: LiAlH4 / diethyl ether 3.1: 13.2 g / PBr3 4.1: 99 percent / 7 h / Heating 5.1: MeONa / methanol / 3 h / Heating 5.2: 85 percent / methanol / Heating View Scheme