Ethanol → {3-methoxy-4-[(1-methyl-4-phenyl-1H-imidazol-2-yl)methoxy]phenyl}methanol

HRID 2221577Notes

Reaction equation

HRID 2221577 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]([CH3:24])[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)[CH:6]=[O:7].C(O)C.[BH4-].[Na+].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]([CH3:24])[CH:15]=[C:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 866057173-methoxy-4-[(1-methyl-4-phenyl-1H-imidazol-2-yl)methoxy]benzaldehyde

Product 1

HCID 69216914{3-methoxy-4-[(1-methyl-4-phenyl-1H-imidazol-2-yl)methoxy]phenyl}methanolYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-4-[(1-methyl-4-phenyl-1H-imidazol-2-yl)methoxy]benzaldehyde (1.37 g) in tetrahydrofuran (50 mL)-ethanol (10 mL) was gradually added sodium borohydride (0.16 g) at room temperature, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture and the precipitated crystals were collected by filtration to give {3-methoxy-4-[(1-methyl-4-phenyl-1H-imidazol-2-yl)methoxy]phenyl}methanol as colorless crystals (1.15 g, yield 85%). Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 126-127° C.

Workup

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

Sources & evidence

ORD record
ord-e85e05d1c6c74d48a9d8475d1e45e57f
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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