2,4,6-Trimethylpyridine → 5-(5-Oxocyclopent-1-en-1-yl)pentyl acetate

Participants

Reaction Steps

161 g [0.76 mol ] of 2-(5-acetoxypentyl)-cyclopentanone were dissolved in 440 ml of carbon tetrachloride, and a solution of 76 ml [0.935 mol] of sulfuryl chloride in 75 ml of carbon tetrachloride was added dropwise, while stirring at 10°-15° C., and the whole was stirred for 4 hours at room temperature. The solvent was distilled off under reduced pressure, the residue dissolved in toluene, washed with water and bicarbonate solution and dried over magnesium sulfate. 150 ml [1.25 mols] of 2,4,6-trimethylpyridine were added to the filtered solution, which was then refluxed, while stirring, for 15 hours. After cooling, the solution was washed twice with 2 n HCl, once with water and once with sodium bicarbonate solution, dried over sodium sulfate, filtered, and the solvent was distilled off under reduced pressure. The residue was distilled under a reduced pressure of 0.5 mm in a column having a length of 10 cm, and 106 g having a boiling point of 120°-125° C. at 0.5 mm Hg were obtained.

Provenance & Evidence