Methanol → [4-(2-Methylimidazol-1-yl)phenyl]methanol

HRID 1108063Notes

Reaction equation

HRID 1108063 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:17]=[CH:16][C:10]([C:11](OCC)=[O:12])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[H-].C([Al+]CC(C)C)C(C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[CH3:1][C:2]1[N:3]([C:7]2[CH:17]=[CH:16][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9357Potassium Sodium TartrateHCID 14664350Ethyl 4-(2-methyl-1H-imidazol-1-yl)benzoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 11735617[4-(2-Methylimidazol-1-yl)phenyl]methanolYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-(2-methylimidazol-1-yl)benzoate (46 g, 0.2 mol) in dry CH2Cl2 (1 l) cooled to -75° C. under a nitrogen atmosphere was added diisobutyl-aluminum hydride (540 ml, 0.93 M in hexane) carefully over 30 minutes and then the mixture was allowed to warm slowly to ambient temperature. After stirring for 5 hours the reaction mixture was cooled in an ice-bath and methanol (30 ml) carefully added. A 30% aqueous solution of Rochelle's salt (500 ml) was then added and the mixture stirred at ambient temperature for 16 hours. Insolubles (essentially product) were removed by filtration and the organic phase separated and washed with water (500 ml), dried (MgSO4) and evaporated. The combined resultant solids were recrystallized from ethanol (ca 300 ml) to afford the titled compound (35.6 g, 95%) as white needles.

Workup

  1. temperaturewas cooled in an ice-bath
  2. stirringthe mixture stirred at ambient temperature for 16 hours
  3. customInsolubles (essentially product) were removed by filtration
  4. customthe organic phase separated
  5. washwashed with water (500 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customwere recrystallized from ethanol (ca 300 ml)

Sources & evidence

ORD record
ord-023c92e845624906a88a32ef8ca33974
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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