Ethyl Acetate → HCID 59260092, compound

HRID 642989Notes

Reaction equation

HRID 642989 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:17])[CH:10]=[C:11]([C:13](OC)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH3:17])[CH:10]=[C:11]([CH2:13][OH:14])[N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59260059HCID 59260059, compound

Product 1

HCID 59260092HCID 59260092, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of methyl 2-(4-iodophenyl)-1-methyl-1H-imidazole-4-carboxylate prepared above (72 mg, 0.21 mmol) in toluene (4 mL), LiAlH4 (61 mg, 1.6 mmol) was added. The mixture was heated at 110° C. overnight. After being cooled to room temperature, EtOAc (15 mL) and 1N aq. NaOH (15 mL) were added. The mixture was filtered through celite. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give (2-(4-iodophenyl)-1-methyl-1H-imidazol-4-yl)methanol (46 mg). MS 315.0 (M+H).

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationThe mixture was filtered through celite
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-578fc4200aff4ba980ba9086c9947bef
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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