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

HRID 617066Notes

Reaction equation

HRID 617066 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 9), 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 magnesium 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 mμ (10700); θmax. = 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 magnesium 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-f9f67bc159c14d59addccca5b2a3962a
Source dataset
uspto-grants-1978_02
Patent number
US04076947

Reaction notes

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