Sodium borohydride → 2-Hydroxymethyl-1-methyl-4-phenyl-5-(4-pyridyl)imidazole

HRID 2293511Notes

Reaction equation

HRID 2293511 reaction equation
[CH:1]([C:3]1[N:4]([CH3:20])[C:5]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:4]([CH3:20])[C:5]([C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 187715342-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

Product 1

HCID 187715292-Hydroxymethyl-1-methyl-4-phenyl-5-(4-pyridyl)imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole (0.830 g, 3.15 mmol) in MeOH at 0° C. was added NaBH4 (0.143 g, 3.78 mmol). The mixture was stirred at rt for 0.5 h when the solvent was evaporated in vacuo and the residue was partitioned between CH2 Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with 25:1 CH2Cl2 /MeOH. The title compound was obtained as a white solid (0.608 g, 73%): mp 236°-238° C.

Workup

  1. customwas evaporated in vacuo
  2. customthe residue was partitioned between CH2 Cl2 and H2O
  3. extractionThe organic extract
  4. washwas washed with aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with 25:1 CH2Cl2 /MeOH

Sources & evidence

ORD record
ord-b3850594892e4053b1c3fb7f35fcc3aa
Source dataset
uspto-grants-1997_11
Patent number
US05686455

Reaction notes

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