Water → Imidazo[1,5-a]pyridin-8-ylmethanol

HRID 1473880Notes

Reaction equation

HRID 1473880 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1[N:8]=[CH:9][N:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](OCC)=[O:17])[C:11]=12.O.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[CH:7]1[N:8]=[CH:9][N:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[C:11]=12

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69160068Ethyl imidazo[1,5-a]pyridine-8-carboxylate

Product 1

HCID 10351843Imidazo[1,5-a]pyridin-8-ylmethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold solution of lithium aluminum hydride (1.62 g, 42.4 mmol, 4.0 eq) in THF (50 mL) was added the crude ethyl imidazo[1,5-a]pyridine-8-carboxylate (2.7 g, 14.2 mmol, 1.0 eq) and the reaction mixture was heated at reflux for 2 h. The reaction was cooled and water (1.7 mL), 15% NaOH (1.7 mL) and water (5.1 mL) were slowly added. Solution was diluted with excess EtOAc and stirred at rt for 30 min. The solution was filtered and the solid was washed with ethyl acetate. Organic layers were combined, dried and solvent was removed to give crude imidazo[1,5-a]pyridine-8-methanol, which was purified by column chromatography (EtOAc/Hexane). MS: exact mass calculated for C8H8N2O, 148.06; m/z found, 149 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureThe reaction was cooled
  4. filtrationThe solution was filtered
  5. washthe solid was washed with ethyl acetate
  6. customdried
  7. customsolvent was removed

Sources & evidence

ORD record
ord-cba0258807c04480ad3c61d97471d7c8
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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