Potassium trimethylsilanolate → [3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic Acid

HRID 2266635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266635
C[O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]2[C:7]=1[C:8]([CH3:25])=[C:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[CH:10]=[N:11]2.C[Si](C)(C)[O-].[K+]>O1CCCC1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:9]2[CH:10]=[N:11][C:12]3[C:7]([C:8]=2[CH3:25])=[C:6]([O:5][CH2:4][C:3]([OH:26])=[O:2])[CH:15]=[C:14]([CH3:16])[CH:13]=3)=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 23668039Potassium trimethylsilanolateHCID 68782397[3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic Acid Methyl Ester

Produkt 1

HCID 57742511[3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of [3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic acid methyl ester (1.8 g), tetrahydrofuran and potassium trimethylsilanolate (0.19 g) was heated at 100° C. in a microwave reactor for 5 minutes. The mixture was concentrated under reduced pressure, diluted with water and acidified by the addition of concentrated hydrochloric acid. The resulting precipitate was collected by filtration and purified by preparative reverse-phase HPLC, using a gradient over 30 minutes of acetonitrile in water (35% to 95% organic modifier) to afford title compound, 0.015 g.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. additionacidified by the addition of concentrated hydrochloric acid
  4. filtrationThe resulting precipitate was collected by filtration
  5. custompurified by preparative reverse-phase HPLC
  6. customover 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-498f70889cdf42a89140fb26f29ca368
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858640B2

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