Sodium Hydroxide → 3-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-ol

HRID 1533056Notes

Reaction equation

HRID 1533056 reaction equation
CC1C=C(C=C(C)C=1)C([O:7][CH2:8][CH2:9][CH:10]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17](=[O:26])[C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=1)=O.[OH-].[Na+]>CO>[Cl:34][C:29]1[CH:28]=[C:27]([CH:10]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17](=[O:26])[C:18]2[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=2)[CH2:9][CH2:8][OH:7])[CH:32]=[CH:31][C:30]=1[Cl:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 226138023-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butyl 3,5-dimethylbenzoate

Product 1

HCID 226138373-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-olYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(3,4-Dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butyl 3,5-dimethylbenzoate (0.93 g) (see Preparation 31) was dissolved in methanol (10 ml) and 2N aqueous sodium hydroxide solution (2 ml) added. A thick gum formed, additional methanol was added (50 ml) and the resulting suspension sired at room temperature overnight. The methanol was then removed under reduced pressure and the residue partitioned between dichloromethane (50 ml) and water (10 ml). The organic phase was separated, washed with brine and the solvent removed under reduced pressure to give the crude product which was chromatographed on silica gel eluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane:methanol, to give 3-(3,4-dichlorophenyl)-4-[2-(3,5-dimethylbenzoyl)imidazol-1-yl]butan-1-ol (0.67 g) as a white foam.

Workup

  1. customA thick gum formed
  2. customThe methanol was then removed under reduced pressure
  3. customthe residue partitioned between dichloromethane (50 ml) and water (10 ml)
  4. customThe organic phase was separated
  5. washwashed with brine
  6. customthe solvent removed under reduced pressure
  7. customto give the crude product which
  8. customwas chromatographed on silica gel eluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane

Sources & evidence

ORD record
ord-3c2cb5d0c2f043a6b95a3d863c07e172
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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