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Sodium Hydroxide → HCID 9817284, Verbindung

HRID 1937336
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1937336
[CH2:1]([S:8]([CH2:10][CH:11]([CH2:22][CH2:23][C:24]([O:26]CC1C=CC=CC=1)=[O:25])[C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[CH2:1]([S:8]([CH2:10][CH:11]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:12]([OH:14])=[O:13])=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22460508Dibenzyl 2-[(benzylsulfinyl)methyl]pentanedioate

Produkt 1

HCID 9817284HCID 9817284, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled solution (5° C.) of dibenzyl 2-[(benzylsulfinyl)methyl]pentanedioate (15.2 g, 33.9 mmol) in tetrahydrofuran (750 mL) was added 0.1 N NaOH (745 mL, 74.5 mmol NaOH) with stirring. The cloudy reaction mixture was allowed to warm to room temperature. After 16 hours, the reaction mixture had become homogenous. The solution was concentrated under reduced pressure to remove the tetrahydrofuran. The remaining aqueous solution was washed with ethyl acetate, then made acidic (pH 1) with concentrated HCl. The mixture was extracted twice with ethyl acetate. The ethyl acetate was removed under reduced pressure and the resulting waxy solid was purified by column chromatography to yield 6.9 g (76%) of white solid.

Aufarbeitung

  1. customThe cloudy reaction mixture
  2. concentrationThe solution was concentrated under reduced pressure
  3. customto remove the tetrahydrofuran
  4. washThe remaining aqueous solution was washed with ethyl acetate
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. customThe ethyl acetate was removed under reduced pressure
  7. customthe resulting waxy solid was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d6f28cdd755d47378d59c62341b937f8
Quelldatensatz
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06395718B1

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