Triethylamine → Pentadecalactone

Participants

Reaction Steps

To a refluxing solution of 510 mg (2.0 mmol) of 2-chloro-1-methylpyridinium iodide in 50 ml of toluene, there was added a solution of 134 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 404 mg (4.0 mmol) of triethylamine in 40 ml of toluene over a period of 8 hours at a continuous and uniform rate and the reaction mixture was refluxed for and additonal 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 1,15 -pentadecanolide was obtained in 63%. yield.

Provenance & Evidence