StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

5-Thiazolecarboxylic acid, 2-methyl- → 2-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acid

HRID 1923581
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1923581
[CH3:1][C:2]1[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=1.[Li]CCCC.[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:26]([CH:27]=[O:28])=[C:25]([CH3:29])[O:24][N:23]=2)=[N:20][CH:21]=1>C1COCC1>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:26]([CH:27]([OH:28])[CH2:1][C:2]3[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=3)=[C:25]([CH3:29])[O:24][N:23]=2)=[N:20][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 988455-Thiazolecarboxylic acid, 2-methyl-HCID 866472723-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 666436562-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acidAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a stirred solution of 2-methyl-thiazole-5-carboxylic acid (1.15 g, 8.05 mmol) in THF (67 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 10.06 mL, 16.1 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde (1.66 g, 8.05 mmol) in THF (24 mL) was added dropwise. After 3 h the reaction mixture was quenched with citric acid solution (5%, 50 mL) then warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, water, dried over sodium sulfate, filtered and concentrated. Purification by trituration (ethyl acetate) afforded the title compound (1.85 g, 66%) as a light yellow solid. MS: m/e=348.2 [M−H]−.

Aufarbeitung

  1. customAfter 3 h the reaction mixture was quenched with citric acid solution (5%, 50 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine, water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by trituration (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-70c6b216fa2e4510bec1273ad2f673ea
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178522B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion