6-(4-Pyridinyl)-5-hexyn-1-ol → 6-(4-Pyridinyl)-5-hexyn-1-ol

Participants

Reaction Steps

A solution of 6-(4-pyridinyl)-5-hexyn-1-ol (2.36 g, 13.47 mmol) in acetic acid (25 ml) was hydrogenated over platinum (IV) oxide (0.612 g, 2.69 mmol) for 72 hours. The mixture was filtered through a Celite cartridge, washed through with acetic acid and then ethyl acetate. The combined filtrate and washings were evaporated in vacuo to give a dark brown oil. The mixture was hydrogenated again as before, this time in 100 ml acetic acid for 20 hours. The mixture was filtered through a Celite cartridge, washed through with acetic acid and then ethyl acetate. The combined filtrate and washings were evaporated in vacuo to give a dark brown oil. The sample was loaded in methanol and eluted on aminopropyl (NH2) 70 g using MeOH. The solvent evaporated in vacuo to give the title compound contaminated with 10% 6-(4-pyridinyl)-5-hexyn-1-ol as a dark brown gum (2.94 g).

Provenance & Evidence