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

HRID 2051783Notes

Reaction equation

HRID 2051783 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])(=[O:3])[CH3:2].S(Cl)(Cl)(=O)=O.CC1C=C(C)C=C(C)N=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 24648Sulfuryl chlorideHCID 131315305-(2-Oxocyclopentyl)pentyl acetate

Product 1

HCID 132897885-(5-Oxocyclopent-1-en-1-yl)pentyl acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

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.

Workup

  1. stirringthe whole was stirred for 4 hours at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue dissolved in toluene
  4. washwashed with water and bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. temperaturewas then refluxed
  7. stirringwhile stirring, for 15 hours
  8. temperatureAfter cooling
  9. washthe solution was washed twice with 2 n HCl, once with water and once with sodium bicarbonate solution
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. distillationthe solvent was distilled off under reduced pressure
  13. distillationThe residue was distilled under a reduced pressure of 0.5 mm in a column
  14. customwere obtained

Sources & evidence

ORD record
ord-5b929fa1346146a3b9e7009be9e5e953
Source dataset
uspto-grants-1980_01
Patent number
US04182773

Reaction notes

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