Sodium Hydroxide → HCID 22613811, compound

HRID 844575Notes

Reaction equation

HRID 844575 reaction equation
C1C2C(=CC=CC=2)C=CC=1C([O:13][CH2:14][CH2:15][CH:16]([C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=1)[CH2:17][N:18]1[CH:22]=[CH:21][N:20]=[C:19]1[C:23]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)=[O:24])=O.[OH-].[Na+]>O1CCOCC1>[Cl:42][C:37]1[CH:36]=[C:35]([CH:16]([CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[C:19]2[C:23]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[O:24])[CH2:15][CH2:14][OH:13])[CH:40]=[CH:39][C:38]=1[Cl:41]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22613842HCID 22613842, compound

Product 1

HCID 22613811HCID 22613811, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(3,4-Dichlorophenyl)-4-[2-(2-naphthoyl)imidazol-1-yl]butyl 2-naphthoate (1.25 g) (see Preparation 42) was dissolved in 1,4-dioxane (15 ml), 1N aqueous sodium hydroxide solution (4 ml) added and the mixture stirred at room temperature overnight. The dioxane was then removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was separated, washed sequentially with 1N aqueous sodium hydroxide solution, water and 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-(2-naphthoyl)imidazol-1-yl]butan-1-ol (0.8 g) as a gum.

Workup

  1. customThe dioxane was then removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed sequentially with 1N aqueous sodium hydroxide solution, water and brine
  5. customthe solvent removed under reduced pressure
  6. customto give the crude product which
  7. 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-61c667a474374aba8797b9645359c229
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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