Sodium Hydroxide → 4-Hydroxymethyl-1-propylimidazole

HRID 70357Notes

Reaction equation

HRID 70357 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:10]1[CH:14]=[C:13]([CH:15]=[O:16])[N:12]=[CH:11]1)[CH2:8][CH3:9].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH2:7]([N:10]1[CH:14]=[C:13]([CH2:15][OH:16])[N:12]=[CH:11]1)[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 103517661-Propyl-1H-imidazole-4-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 124932744-Hydroxymethyl-1-propylimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of LAH (2.0 M in THF, 1.9 ml, 3.882 mmol) in THF (10 ml) was added dropwise a solution of 1-propyl-1H-imidazole-4-carbaldehyde (487 mg, 3.529 mmol) in THF (4 ml) at 0° C. After stirred at 0° C. for 5 min, water (0.2 ml), 15% NaOH (0.2 ml) was added dropwise to the reaction mixture under 0° C. The mixture was further stirred at room temperature for 2 hours. MgSO4 was added to the mixture and the solid was filtered away and the filtrate was concentrated in vacuo to get a yellow oil and used without further purification.

Workup

  1. stirringThe mixture was further stirred at room temperature for 2 hours
  2. filtrationthe solid was filtered away
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto get a yellow oil
  5. customused without further purification

Sources & evidence

ORD record
ord-7ee23ddae7fd417294e602b496193419
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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