Water → HCID 22342671, compound

HRID 584171Notes

Reaction equation

HRID 584171 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9](OCC)=[O:10])[N:4]=[CH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][OH:10])[N:4]=[CH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22342827HCID 22342827, compound

Product 1

HCID 22342671HCID 22342671, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of ethyl 3-(1-methyl-1H-imidazol-4-yl)propionate (2.63 g) in tetrahydrofuran (26 ml) was added lithium aluminum hydride (0.55 g) by small-portions under nitrogen atmosphere. After the mixture was stirred for 0.5 hour, water and 15% aqueous sodium hydroxide solution were added successively to the mixture. The resulting precipitates were filtrated off through Celite pad and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine successively, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using dichloromethane-methanol (100:1) as eluent to give 3-(1-methyl-1H-imidazol-4-yl)-1-propanol (940 mg).

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtrated off through Celite pad
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine successively
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a45dfc2405d94fea91d3841a4557eb91
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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