Water → 3-(1H-Imidazol-4-yl)-1-propanol

HRID 870607Notes

Reaction equation

HRID 870607 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14](OC)=[O:15])[N:9]=[CH:8]1.O.[OH-].[Na+]>O1CCCC1>[NH:9]1[C:10]([CH2:12][CH2:13][CH2:14][OH:15])=[CH:11][N:7]=[CH:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178500031HCID 178500031, compound

Product 1

HCID 5727003-(1H-Imidazol-4-yl)-1-propanolYield 279.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add lithium aluminum hydride (1M in tetrahydrofuran; 17 mL; 2.0 equiv; 17.00 mmoles) dropwise over 5 minutes to a 0° C. solution of methyl 3-(1H-imidazol-4-yl)propanoate (2.2 g; 1.0 equiv; 8.52 mmoles) in tetrahydrofuran (85 mL). Warm the reaction mixture to ambient temperature and stir for 16 hours. Add water (0.65 mL), 15% sodium hydroxide (0.65 mL), and water (1.95 mL) sequentially, then stir for 30 minutes. Filter the resulting solid and rinse with acetone. Concentrate the filtrate to afford 3-(1H-imidazol-5-yl)propan-1-ol (3.0 g; 61%) as a white solid. To further purify the product, suspend a portion of 3-(1H-imidazol-4-yl)propan-1-ol (1.5 g) in water (50 mL) and stir at 100° C. for 2 hours. Filter the product mixture and concentrate the filtrate to afford pure 3-(1H-imidazol-5-yl)propan-1-ol (0.5 g) as an off white solid: MS (m/z): 127(M+1).

Workup

  1. filtrationFilter the resulting solid
  2. washrinse with acetone
  3. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-440cba86ce294c03baa991b214031952
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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