Ethanol → (5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methanol

HRID 83920Notes

Reaction equation

HRID 83920 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15]([CH:24]=[O:25])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)C.[BH4-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C:15]([CH2:24][OH:25])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 866622355-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-carbaldehyde

Product 1

HCID 66740712(5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methanolYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-carbaldehyde (740 mg, 1.96 mmol) in anhyd ethanol (15 mL) was added NaBH4 (91 mg, 2.4 mmol). After stirring 3 h, the mixture was poured into water, and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo to give (5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methanol as a white solid (670 mg, 88% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5bd1aa4e3f0446fa140d6fe154680d1
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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