Diethyl Ether → Imidazo[1,2-a]pyridin-8-ylmethanol

HRID 1473885Notes

Reaction equation

HRID 1473885 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10](OC)=[O:11])[C:5]=12.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC>C1COCC1.C(OCC)(=O)C>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][OH:11])[C:5]=12

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 15098894Methyl imidazo[1,2-a]pyridine-8-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11029987Imidazo[1,2-a]pyridin-8-ylmethanolYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold solution of methyl imidazo[1,2-a]pyridine-8-carboxylate (5.55 g, 31.53 mmol, 1 eq) in THF (100 mL) was added LAH in ether (1 M solution in ether, 4 equiv.) and then stirred at rt for 6 h. The reaction mixture was cooled to 0° C. and quenched with water/15% NaOH/water. Reaction mixture was diluted with ethyl acetate and stirred at room temperature for 15 min and then filtered. The solid was washed with ethanol and the organic layers were combined, dried and evaporated to give the alcohol, which was purified by column chromatography to yield the desired product in 40% yield.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with water/15% NaOH/water
  3. customReaction mixture
  4. stirringstirred at room temperature for 15 min
  5. filtrationfiltered
  6. washThe solid was washed with ethanol
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-c3d3e44f0bc74ff69c955d2c85e48ae7
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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