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Water → (3-Ethynyl-quinolin-6-yloxy)-metoxy-acetic acid

HRID 1962858
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1962858
C[O:2][C:3](=[O:24])[CH:4]([O:22][CH3:23])[O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[C:17][Si](C)(C)C)=[CH:9]2.[OH-].[Na+].C(OCC)(=O)C.O>C(O)C>[C:16]([C:10]1[CH:11]=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][C:6]([O:5][CH:4]([O:22][CH3:23])[C:3]([OH:24])=[O:2])=[CH:15][CH:14]=2)#[CH:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59565426Methoxy-(3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetic acid methyl ester

Produkt 1

HCID 59565329(3-Ethynyl-quinolin-6-yloxy)-metoxy-acetic acidAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

To a solution of methoxy-(3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetic acid methyl ester (1.99 g) in ethanol (14 mL) was added a solution of sodium hydroxide 2N (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added. The mixture was stirred. The two layers were separated. The aqueous layer was acidified at pH 1 with HCl 2N. Then it was extracted with ethyl acetate (twice). The organic layer was dried over sodium sulphate, filtered and concentrated under reduced pressure to give (3-ethynyl-quinolin-6-yloxy)-metoxy-acetic acid (1.15 g) as an orange solid.

Aufarbeitung

  1. stirringThe mixture was stirred
  2. customThe two layers were separated
  3. extractionThen it was extracted with ethyl acetate (twice)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-306f31706ec64ccca1802d314cdfb384
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415272B2

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