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Lithium Hydroxide → HCID 59577007, Verbindung

HRID 2041978
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2041978
[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:18])[C:13]([O:15]CC)=[O:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C(O)C>[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:12](=[O:18])[C:13]([OH:15])=[O:14])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 59577194HCID 59577194, Verbindung

Produkt 1

HCID 59577007HCID 59577007, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of ethyl 2-(3-(2-tert-butylphenoxy)azetidin-1-yl)-2-oxoacetate (1.65 g, 5.40 mmol) in ethanol (60.0 ml) was added lithium hydroxide (16.2 mL of 1.0 M solution in water, 16.2 mmol) at room temperature. After 1 h the reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with water, cooled to 0° C., adjusted to about pH 1 with 1.0 N hydrochloric acid and the resulting solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was recrystallized from heptane/ethyl acetate to provide 2-(3-(2-tert-butylphenoxy)azetidin-1-yl)-2-oxoacetic acid (0.97 g, 65%) as a white powder.

Aufarbeitung

  1. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with water
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a5ad544785d34beb93db8da0dae66deb
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586571B2

Notizen zur Reaktion

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