Sodium Hydroxide → 2-(1h-imidazol-1-yl)propan-1-ol

HRID 1859824Notes

Reaction equation

HRID 1859824 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH:12]([CH3:18])[C:13](OCC)=[O:14])[CH:11]=[CH:10][N:9]=[CH:8]1.[OH-].[Na+]>C1COCC1>[N:7]1([CH:12]([CH3:18])[CH2:13][OH:14])[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18626501ethyl 2-(1H-imidazol-1-yl)propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1091472-(1h-imidazol-1-yl)propan-1-olYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 16.6 g (0.437 mol) of lithium aluminum hydride in 700 mL of THF was warmed to 40° C. and treated dropwise with 36.8 g (0.219 mol) of ethyl 2-(1H-1-imidazolyl)propanoate and the suspension allowed to stir at room temperature for 2.5 hours. The mixture was decomposed with dilute NaOH, filtered, and the solid washed with THF. The solvent was removed under reduced pressure and the residue distilled at 155-170° C./0.5 mm Hg. There was obtained 18.6 g (67% yield) of the product as an oil. The structure was confirmed by NMR and mass spectroscopy. MS m/z 127 (M+H+).

Workup

  1. filtrationfiltered
  2. washthe solid washed with THF
  3. customThe solvent was removed under reduced pressure
  4. distillationthe residue distilled at 155-170° C./0.5 mm Hg

Sources & evidence

ORD record
ord-e379ee8055ab4ae7819c5a9868492517
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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