Methanol → 7-(3-Methoxy-5-oxocyclopent-1-EN-1-YL)heptanoic acid

HRID 225351

Reaktionsgleichung

Reaktionsgleichung von HRID 225351
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.N1C(C)=CC=CC=1C.[CH3:25][OH:26]>[B-](F)(F)(F)F.[Ag+]>[CH3:25][O:26][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

5

Edukt 3

HCID 887Methanol2×HCID 79372,6-LutidineHCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Produkt 1

HCID 233300047-(3-Methoxy-5-oxocyclopent-1-EN-1-YL)heptanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 159722Silver tetrafluoroborateKatalysator

Versuchsvorschrift

To a stirred solution of 5.30 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 85ml. of methanol at 0°-3° C. is added 4.40 g. (22.6 mmole) of silver fluoborate in one portion. After 2 minutes, the mixture is treated with 2.66 g. (24.8 l mmoles) of 2,6-lutidine. After stirring for 30 minutes at 0°-3° C. the mixture is stirred at ambient temperature for 45 minutes. Silver bromide is removed by filtration, and the filtrate is concentrated to a volume of 40 ml. The solution is treated with saturated sodium chloride solution and extracted with ether. The extract is washed successively with 0.5 N hydrochloric acid solution, water, and saturated sodium chloride solution; dried over magnesium sulfate; and concentrated. Partition chromatography of the residue on Celite gives an oil, λmax.MeOH =220 mμ (7450); νmax.=1715 (carbonyl groups) and 1095 cm-1 (methoxy group).

Aufarbeitung

  1. additionthe mixture is treated with 2.66 g
  2. stirringis stirred at ambient temperature for 45 minutes
  3. customSilver bromide is removed by filtration
  4. concentrationthe filtrate is concentrated to a volume of 40 ml
  5. additionThe solution is treated with saturated sodium chloride solution
  6. extractionextracted with ether
  7. washThe extract is washed successively with 0.5 N hydrochloric acid solution, water, and saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationand concentrated
  10. customPartition chromatography of the residue on Celite
  11. customgives an oil, λmax

Quellen und Nachweise

ORD-Eintrag
ord-9964a853461340b797a30370fb59136b
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04236027

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