3,5-dimethyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester → HCID 66601738, Verbindung

HRID 220470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220470
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:13]([CH3:24])=[N:14][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:16]=1[CH3:17])=O)C>O1CCCC1>[CH3:24][C:13]1[C:12]([CH2:10][OH:9])=[C:16]([CH3:17])[N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:14]=1

Komponenten

4

Edukt 2

HCID 98562563,5-dimethyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 66601738HCID 66601738, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Suspend lithium aluminum hydride (0.359 g, 9.46 mmol) in tetrahydrofuran (25 mL) at −10° C. and add 3,5-dimethyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester (1.160 g, 4.73 mmol) dropwise in tetrahydrofuran (5 mL). Allow the mixture to warm to 25° C. and stir for 4 hr. Cool the mixture to 0° C. then quench carefully with saturated sodium sulfate solution (1 mL). Allow the mixture to stir at room temperature for 2 hr. then filter off the precipitate, dry the solution and concentrate to give (3,5-dimethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol as a yellow solid (0.821 g, 86%). 1H-NMR (400 MHz, DMSO) 8.408 (m, 1H); 7.889 (m, 1H); 7.738 (m, 1H); 7.256 (m, 1H); 4.269 (s, 2H); 2.459 (s, 3H); 2.181 (s, 3H)

Aufarbeitung

  1. customat −10° C.
  2. temperatureCool the mixture to 0° C.
  3. customthen quench carefully with saturated sodium sulfate solution (1 mL)
  4. stirringAllow the mixture to stir at room temperature for 2 hr
  5. filtrationthen filter off the precipitate
  6. customdry the solution
  7. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-b820d37f05d8476ba55d0f84e0c98875
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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