Ethylene Glycol → 7-[3-(2-Hydroxyethoxy)-5-oxocyclopent-1-EN-1-YL]heptanoic acid

HRID 225353

Reaction equation

HRID 225353 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]([OH:16])=[O:15])=[CH:3]1.[CH2:17]([OH:20])[CH2:18][OH:19].N1C(C)=CC=CC=1C.CO>O.[B-](F)(F)(F)F.[Ag+]>[OH:19][CH2:18][CH2:17][O:20][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]([OH:16])=[O:15])=[CH:3]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 887MethanolHCID 79372,6-LutidineHCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Product 1

HCID 233299417-[3-(2-Hydroxyethoxy)-5-oxocyclopent-1-EN-1-YL]heptanoic acid

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 19.1 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 310 ml. of ethylene glycol is added 15.6 g. (80 mmole) of silver fluoborate during 2 minutes. The exothermic reaction is controlled to give a temperature of 29° C., and after 1 minute the mixture is treated during 1 minute with 8.6 g. (λmmole) of 2,6-lutidine. The mixture is stirred at ambient temperature for 2 hours, diluted with water, and filtered. The filtrate is diluted with saturated sodium chloride solution and extracted with ether. The extract is washed with half-saturated sodium chloride solution containing a little hydrochloric acid and saturated sodium chloride solution. The extract is dried over magnesium sulfate and concentrated. Column chromatography of the residue on silica gel gives an oil, λmax.MeOH =216 mμ(8350); νmax.=3340 (hydroxyl groups), 1700 (carbonyl groups), and 1620 cm-1 (olefin group).

Workup

  1. customThe exothermic reaction
  2. customto give a temperature of 29° C.
  3. additionafter 1 minute the mixture is treated during 1 minute with 8.6 g
  4. filtrationfiltered
  5. additionThe filtrate is diluted with saturated sodium chloride solution
  6. extractionextracted with ether
  7. washThe extract is washed with half-saturated sodium chloride solution
  8. additioncontaining a little hydrochloric acid and saturated sodium chloride solution
  9. dry with materialThe extract is dried over magnesium sulfate
  10. concentrationconcentrated
  11. customColumn chromatography of the residue on silica gel gives an oil, λmax

Sources & evidence

ORD record
ord-60f3cfbf064447df9c0fc0c84d03b4c7
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Linked notes

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