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Pyrazole → [3-(1H-Pyrazol-1-yl)phenyl]acetic acid

HRID 15784
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 15784
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[C@@H]1(N)CCCC[C@H]1N.CCCCCCCCCCCC.Br[C:33]1[CH:34]=[C:35]([CH2:39][C:40]([OH:42])=[O:41])[CH:36]=[CH:37][CH:38]=1.[OH-].[Na+]>O1CCOCC1.[Cu]I>[N:1]1([C:33]2[CH:34]=[C:35]([CH2:39][C:40]([OH:42])=[O:41])[CH:36]=[CH:37][CH:38]=2)[CH:5]=[CH:4][CH:3]=[N:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 1048PyrazoleHCID 8182DodecaneHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 438061,2-Diaminocyclohexane, trans-HCID 74653(3-Bromophenyl)acetic acid

Produkt 1

HCID 21062671
[3-(1H-Pyrazol-1-yl)phenyl]acetic acid
Ausbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Pyrazole (1.2 eq), Cs2CO3 (2.5 eq), CuI (0.5 eq), trans-1,2-cyclohexanediamine (0.6 eq) and dodecane (1 eq), were added to a stirred solution of 3-bromophenylacetic acid (1 eq) in dioxane at room temperature under an inert atmosphere. The mixture was irradiated in a microwave reactor (PersonalChemistry Emrys™ Optimiser, 300 W, 160° C., 20 min), then added to a 1N aqueous solution of NaOH, and extracted with Et2O. The aqueous phase was acidified to pH=3 with HCl 2N, then extracted with ethyl acetate; this phase was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (Silica) eluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1, affording the title compound in 65% yield.

Aufarbeitung

  1. customThe mixture was irradiated in a microwave reactor (PersonalChemistry Emrys™ Optimiser, 300 W, 160° C., 20 min)
  2. extractionextracted with Et2O
  3. extractionextracted with ethyl acetate
  4. washthis phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customThe crude material was purified on SPE cartridge (Silica)
  8. washeluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-0a2d14e5ae3c4320bcb0991c6c6eb791
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07732600B2

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