1: 6-N,N-dibutylaminonaphthyl-(1)-methyltriphenylphosphonium bromide With sodium methylate in methanol 3 h; Heating; 2: pyridine-3-aldehyde in methanol Heating;

1.1: 78 percent / pyridine / 72 h / 220 °C 2.1: 100 percent / NaOH / pentan-1-ol / 72 h / 170 °C 3.1: LiAlH4 / diethyl ether 4.1: 13.2 g / PBr3 5.1: 99 percent / 7 h / Heating 6.1: MeONa / methanol / 3 h / Heating 6.2: 85 percent / methanol / Heating 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

1.1: 99 percent / 7 h / Heating 2.1: MeONa / methanol / 3 h / Heating 2.2: 85 percent / methanol / Heating View Scheme

1.1: 13.2 g / PBr3 2.1: 99 percent / 7 h / Heating 3.1: MeONa / methanol / 3 h / Heating 3.2: 85 percent / methanol / Heating View Scheme

1.1: LiAlH4 / diethyl ether 2.1: 13.2 g / PBr3 3.1: 99 percent / 7 h / Heating 4.1: MeONa / methanol / 3 h / Heating 4.2: 85 percent / methanol / Heating View Scheme