Cyclohexanone, 3,3-dimethyl- → 3,3-dimethyl-1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

HRID 1778935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778935
[Li]CCCC.[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]1.[CH3:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[CH2:15]1>O1CCCC1.CCOCC>[CH3:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]([CH2:6][N:7]2[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]2)([OH:20])[CH2:15]1

Komponenten

6

Edukt 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 1365021,5-DimethylpyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 866813303,3-dimethyl-1-((5-methyl-1H-pyrazol-1-yl)methyl)cyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold (−78° C.) solution of nBuLi (12.48 mL) in tetrahydrofuran (40 mL) was added a solution of 1,5-dimethyl-1H-pyrazole (3.0 g) in tetrahydrofuran (3 mL) dropwise. After stirring for 1 hour, a solution of 3,3-dimethylcyclohexanone (3.94 g) in tetrahydrofuran (3 mL) was added dropwise, and the reaction was allowed to warm to 0° C. After stirring for 1 hour, the reaction mixture was diluted with ether (100 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography, eluting with a gradient of 3% to 25% ethyl acetate in hexanes, gave the title compound.

Aufarbeitung

  1. stirringAfter stirring for 1 hour
  2. washwashed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by silica gel chromatography
  7. washeluting with a gradient of 3% to 25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ead138bcae7344b19599ffd9d4595adb
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266877B2

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