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

HRID 1615668Notes

Reaction equation

HRID 1615668 reaction equation
[N:1]1[C:2]([C:10](OCC)=[O:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[N:1]1[C:2]([CH2:10][OH:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 962WaterHCID 818807Ethyl imidazo[1,2-a]pyridine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2795540Imidazo[1,2-a]pyridin-2-ylmethanolYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold solution of ethyl imidazo[1,2-a]pyridine-2-carboxylate (6.1 g, 32 mmol) in dry THF (300 mL) was added lithium aluminium hydride (LAH) (2.4 g, 64 mmol) in portions, and the temperature was maintained at <5° C. for 2 h. THF and water (50 mL, 1:1 v/v) were added slowly and the mixture was filtered. The filtrate was evaporated to dryness. The residue was re-dissolved in EtOAc (60 mL), and washed with brine (10 mL×3). The organic layers were combined, and the solvent was removed to give the title compound (4.3 g, yield 90%). ESI MS: m/z 149 [M+H]+.

Workup

  1. temperaturethe temperature was maintained at <5° C. for 2 h
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness
  4. dissolutionThe residue was re-dissolved in EtOAc (60 mL)
  5. washwashed with brine (10 mL×3)
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-777e2ad97cab418aa4a24cc93427b57e
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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