Water → Imidazo[1,2-a]pyridin-6-ylmethanol

HRID 1440235

Reaktionsgleichung

Reaktionsgleichung von HRID 1440235
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:5]=12.[BH4-].[Na+].O.ClCCl.CO>CO>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=12

Komponenten

6

Edukt 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 7164582Imidazo[1,2-a]pyridine-6-carbaldehydeHCID 21226129Dichloromethane methanol

Produkt 1

HCID 7060530Imidazo[1,2-a]pyridin-6-ylmethanolAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

0.90 g of the 6-imidazo[1,2-a]pyridinecarbaldehyde prepared in the Preparative Example 5 was dissolved in 20 ml of methanol. The obtained solution was stirred under cooling with ice, followed by the addition of 90 mg of sodium borohydride. The obtained mixture was stirred for 50 minutes, followed by the addition of water. The obtained mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1 to 10:1) to give 0.52 g of the title compound as a faintly orange-yellow solid (yield: 57%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred for 50 minutes
  3. extractionThe obtained mixture was extracted with chloroform
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe obtained residue was purified by silica gel column chromatography [solvent

Quellen und Nachweise

ORD-Eintrag
ord-41af41c29e0942c9ae91c5ee99e256c0
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498634

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