HCID 22613814, compound → HCID 22613805, compound

HRID 1533059Notes

Reaction equation

HRID 1533059 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][CH:32]=[CH:31][C:4]=1[C:5]([C:7]1[N:8]([CH2:12][CH:13]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH2:14][CH2:15][O:16]C2CCCCO2)[CH:9]=[CH:10][N:11]=1)=[O:6]>CO>[Cl:30][C:25]1[CH:24]=[C:23]([CH:13]([CH2:12][N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[C:5](=[O:6])[C:4]2[CH:31]=[CH:32][CH:33]=[CH:34][C:3]=2[O:2][CH3:1])[CH2:14][CH2:15][OH:16])[CH:28]=[CH:27][C:26]=1[Cl:29]

Participants

3

Reactant 1

HCID 22613814HCID 22613814, compound

Product 1

HCID 22613805HCID 22613805, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[2-(2-Methoxybenzoyl)imidazol-1-yl]-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (1.1 g) (see Preparation 57) was dissolved in methanol (20 ml), Amberlyst 15 (trade mark) ion-exchange resin (0.11 g) added and the mixture stirred at room temperature for 5 days. The resin was removed by filtration through a short column of Arbacel (trade mark) filter aid and the solvent removed from the filtrate under reduced pressure to give a residue. This was chromatographed on silica gel eluting with 97:3, by volume, dichloromethane:methanol to give 3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)-imidazol-1-yl]butan-1-ol (0.31 g) as a white foam.

Workup

  1. customThe resin was removed by filtration through a short column of Arbacel (trade mark)
  2. filtrationfilter aid
  3. customthe solvent removed from the filtrate under reduced pressure
  4. customto give a residue
  5. customThis was chromatographed on silica gel eluting with 97:3, by volume, dichloromethane

Sources & evidence

ORD record
ord-4a9c484e3523419b956d1d56e32e781c
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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