Cyclooctanone → 1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclooctanol

HRID 336613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336613
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]1.[C:13]1(=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O1CCCC1>[CH3:12][C:11]1[N:7]([CH2:6][C:13]2([OH:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 10403CyclooctanoneHCID 1365021,5-DimethylpyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 866812711-((5-methyl-1H-pyrazol-1-yl)methyl)cyclooctanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a cold (−78° C.) solution of n-butyllithium (10 mL, 2.5M) in tetrahydrofuran (20 mL) was added 1,5-dimethyl-1H-pyrazole (2.0 g) in tetrahydrofuran (10 mL) dropwise via syringe. After 1 hour, cyclooctanone (2.63 g) in tetrahydrofuran (5 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature. The mixture was quenched by the addition of saturated ammonium chloride solution and ethyl acetate. The layers were separated and the aqueous layer was extracted twice with additional ethyl acetate. The combined organics were dried over Na2SO4, filtered, and concentrated to provide the title compound.

Aufarbeitung

  1. customThe mixture was quenched by the addition of saturated ammonium chloride solution and ethyl acetate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with additional ethyl acetate
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2ee156e0504b4829b44c46e22f549efd
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889675B2

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