Ethanol → (1-Methyl-4-phenyl-1H-imidazol-2-yl)-methanol

HRID 2221576Notes

Reaction equation

HRID 2221576 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH:13]=[O:14].C(O)C.[BH4-].[Na+].O>O1CCCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 145989821-Methyl-4-phenyl-1H-imidazole-2-carboxaldehyde

Product 1

HCID 23076602(1-Methyl-4-phenyl-1H-imidazol-2-yl)-methanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-4-phenyl-1H-imidazole-2-carbaldehyde (7.24 g) in tetrahydrofuran (50 mL)-ethanol (10 mL) was gradually added sodium borohydride (1.47 g) at room temperature and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture and the precipitated crystals were collected by filtration to give (1-methyl-4-phenyl-1H-imidazol-2-yl)methanol as colorless crystals (5.71 g, yield 78%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 191-192° C.

Workup

  1. customat room temperature
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-fb6d0d9ce45d448a9f6e7519152c537e
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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