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Diethyl Ether → {3-Ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid

HRID 1767964
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1767964
[Li+].[OH-].C([O:5][C:6](=[O:37])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[S:23][C:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[N:21][C:20]=3[CH3:34])=[CH:14][CH:15]=2)[C:10]([CH2:35][CH3:36])=[CH:9]1)C.C(OCC)C>C1COCC1>[CH2:35]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[S:23][C:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[N:21][C:20]=3[CH3:34])[CH:12]=2)[N:8]([CH2:7][C:6]([OH:37])=[O:5])[CH:9]=1)[CH3:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 3939Lithium Hydroxide2×HCID 69279669{3-Ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

Produkt 1

HCID 11363494{3-Ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acidAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A 1 M aqueous solution of LiOH (2.3 ml, 2.3 mmol) was added to a solution of {3-ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester (577 mg, 1.15 mmol) in THF (6 ml). After stirring for 1 h at ambient temperature, additional 0.58 ml of the 1N LiOH solution were added and the reaction mixture was stirred for further 2.5 h. Diethyl ether (10 ml) was added, the resulting precipitate was filtered off and redissolved in ethyl acetate and 25% aqueous HCl solution (2 ml). The organic layer was washed with water and dried over sodium sulfate. Removal of the solvent under reduced pressure gave 365 mg (0.77 mmol, 67%) {3-ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for further 2.5 h
  2. filtrationthe resulting precipitate was filtered off
  3. dissolutionredissolved in ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-901015731c3b4e7cbb72652a8d89e20d
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07235572B2

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