Sodium hydride → Docos-21-yn-1-ol

Participants

Reaction Steps

Diaminopropane (DAP) (150 ml) at room temperature under nitrogen was stirred and treated with sodium hydride (100%, 13.55 g, 0.56 mol). The resulting solution was then warmed to 70° C. for 1 hour after which time further DAP (30 ml) is added followed by docos-12-ynol (22 g, 0.068 mol). The resulting solution was then left at 70° C. overnight, cooled and poured into water. The aqueous mixture was extracted three times with chloroform, the combined organic dried (MgSO4), filtered and evaporated to leave a pinkish residue. Recrystallisation from methanol gave docos-21-ynol (31) (18.05 g, 84%) as white crystals mp 64°-70° C.

Provenance & Evidence