Sodium Hydroxide → 3-(5-Hydroxypentylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane

HRID 1654241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654241
[C:1]([CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][C:12]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:13]2)[CH2:9]1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[OH:2][CH2:1][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][C:12]3([O:16][CH2:17][CH2:18][O:19]3)[CH2:13]2)[CH2:9]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 228526373-(4-Carboxybutylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane

Produkt 1

HCID 228526963-(5-Hydroxypentylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octaneAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

49.10 g of 3-(4-carboxybutylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane (prepared as described in Preparation 1) in 150 ml of tetrahydrofuran were added dropwise to a suspension of 10.50 g of lithium aluminum hydride in 675 ml of tetrahyarofuran, whilst cooling with ice. The mixture was then heated under reflux for 80 minutes. Upon completion of the reaction, 42 ml of a 4% w/v aqueous solution of sodium hydroxide were added, and the mixture was stirred at room temperature. The resulting precipitate was removed by filtration, and the filtrate was condensed by evaporation under reduced pressure, giving 46.90 g of a residue. On purifying the residue by silica gel column chromatography, 40.10 g of the title compound were obtained as an oil, from the fractions eluted with hexane containing 20-30% by volume of ethyl acetate.

Aufarbeitung

  1. temperaturewhilst cooling with ice
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 80 minutes
  4. additionwere added
  5. customThe resulting precipitate was removed by filtration
  6. customcondensed
  7. customby evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-80b7dee9b4374a499355a78bbdb4027c
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405870

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