Sodium Hydroxide → Imidazo[1,2-a]pyridine-7-methanol

HRID 408570

Reaktionsgleichung

Reaktionsgleichung von HRID 408570
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[N:13]1[CH:12]=[CH:11][N:8]2[CH:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][C:7]=12

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 11051824Imidazo[1,2-a]pyridine-7-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a −78° C. cooled solution of imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (1 eq.) in dry THF was slowly added a solution of LiAlH4 in THF (1M in THF, 2 eq.). The reaction mixture was warmed to 0° C. and stirred for 30 min. The reaction mixture was then poured onto a cooled aqueous solution of NaOH 2N, stirred for 5 min and filtered through a pad of celite. The filtrate was partitioned between water and EtOAc, the organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford imidazo[1,2-a]pyridin-7-yl-methanol which was used as such without further purification.

Aufarbeitung

  1. stirringstirred for 5 min
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate was partitioned between water and EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fcf8591d91854d84b39396c492629ec7
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759334B2

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