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Sodium Hydroxide → 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-3-ylmethanol

HRID 856786
Notes
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Reaction equation

HRID 856786 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH:7]([C:9]1[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=[N:11][CH:10]=1)=[O:8].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[N:11]1[CH:10]=[C:9]([CH2:7][OH:8])[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 111162275,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-3-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 229385385,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-3-ylmethanolYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of aluminum lithium hydride (0.40 g) in THF (30 ml), 3-formyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1.48 g) in. THF (50 ml) was added dropwise at 0° C. The mixture was stirred for 1 hour at 0° C., and water (0.4 ml), 15% aqueous solution of sodium hydroxide (0.4 ml) and water (1.2 ml) were added dropwise to the mixture. The mixture was stirred at room temperature for 18 hours, magnesium sulfate was added to the mixture, and the precipitates were removed by filtration. The solvent was concentrated under reduced pressure, and the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether, to give 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-methanol (1.24 g) as colorless crystals.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. customthe precipitates were removed by filtration
  3. concentrationThe solvent was concentrated under reduced pressure
  4. filtrationthe precipitated crystals were collected by filtration
  5. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-60de4f8d0d5f4457afae3cc8e78afa40
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262185B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes