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

HRID 461262

Reaktionsgleichung

Reaktionsgleichung von HRID 461262
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>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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159722Silver tetrafluoroborateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 19.1 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 93) 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. (80 mmole) 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, λ maxMeOH = 216 mμ (8350); ν max = 3340 (hydroxyl groups), 1700 (carbonyl groups), and 1620 cm -1 (olefin group).

Aufarbeitung

  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, λ maxMeOH = 216 mμ (8350)

Quellen und Nachweise

ORD-Eintrag
ord-299c76bb8720488dafe7131c43c1a356
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04061672

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