Acetone → 9-(3-Hydroxy-5-oxocyclopent-1-EN-1-YL)nonanoic acid

HRID 436125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436125
Br[CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:3]1.CC(C)=[O:21].O.[K+].[Br-]>[B-](F)(F)(F)F.[Ag+].CO>[OH:21][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:3]1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 253877Potassium BromideHCID 204656274-Bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one

Produkt 1

HCID 132897909-(3-Hydroxy-5-oxocyclopent-1-EN-1-YL)nonanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159722Silver tetrafluoroborateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 57.2 g. of crude 4-bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one (Example 1280) in 500 ml. of acetone and 325 ml. of water at 3° C. is added 44.1 g. (0.226 moles) of silver fluoborate during a 15 minute period. The mixture is stirred at 0°-3° C. for 2 hours and filtered. The filtrate is diluted with water, saturated with solid sodium chloride, and extracted with ether. The extract is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Partition chromatography of the residue on Celite gives white crystals, m.p. 58°-66° C., λmax.MeOH = 223 mμ (7800); νmax (KBr) = 3340 (hydroxyl groups), 1705 (carbonyl groups), and 1625 cm-1 (olefin group).

Aufarbeitung

  1. filtrationfiltered
  2. additionThe filtrate is diluted with water, saturated with solid sodium chloride
  3. extractionextracted with ether
  4. washThe extract is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customPartition chromatography of the residue on Celite
  8. customgives white crystals, m.p. 58°-66° C., λmax

Quellen und Nachweise

ORD-Eintrag
ord-b205f5c92cda42f882e0b6d34671bd06
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04007210

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