Acetic Acid → Ethyl 7-[3-(acetyloxy)-5-oxocyclopent-1-EN-1-YL]heptanoate

HRID 436126Notes

Reaction equation

HRID 436126 reaction equation
Br[CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1.[C:19]([OH:22])(=[O:21])[CH3:20]>C([O-])(=O)C.[Ag+].CO>[C:19]([O:22][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1)(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 204655494-Bromo-2-(carbethoxyhexyl)cyclopent-2-en-1-one

Product 1

HCID 13289791Ethyl 7-[3-(acetyloxy)-5-oxocyclopent-1-EN-1-YL]heptanoate

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 51.6 g. (0.137 moles) of crude 4-bromo-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one (Example 1274), 27 g. (0.162 moles) of silver acetate, and 200 ml. of glacial acetic acid is stirred at reflux for 4.5 hours. The mixture is cooled, and solids are removed by filtration. The filtrate is concentrated and extracted with hot hexane. The extract is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over mangesium sulfate, and concentrated to give an oil. The crude product is distilled at reduced pressure to give a liquid, b.p. 152° - 163° C. (0.01 mm); λmax.MeOH = 223 mu (10700); νmax. = 1745 (ester carbonyl groups), 1725 (ketone carbonyl groups), and 1235 cm-1 (acetoxy group).

Workup

  1. additionA mixture of 51.6 g
  2. temperatureat reflux for 4.5 hours
  3. temperatureThe mixture is cooled
  4. customsolids are removed by filtration
  5. concentrationThe filtrate is concentrated
  6. extractionextracted with hot hexane
  7. washThe extract is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  8. dry with materialdried over mangesium sulfate
  9. concentrationconcentrated
  10. customto give an oil
  11. distillationThe crude product is distilled at reduced pressure
  12. customto give a liquid, b.p. 152° - 163° C. (0.01 mm)

Sources & evidence

ORD record
ord-c179385931184ea3afb1c2c7a4567da6
Source dataset
uspto-grants-1977_02
Patent number
US04007210

Reaction notes

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