Water → 2-[1-[4-[4-[[2-[(E)-2-(2,4-difluorophenyl)ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]-1-ethanol

HRID 2084404Notes

Reaction equation

HRID 2084404 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:6]=[CH:7][N:8]=1.[H-].[Na+].Cl[CH2:23][C:24]1[N:25]=[C:26](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[F:38])[O:27][CH:28]=1.O>CN(C=O)C>[F:38][C:32]1[CH:33]=[C:34]([F:37])[CH:35]=[CH:36][C:31]=1/[CH:30]=[CH:29]/[C:26]1[O:27][CH:28]=[C:24]([CH2:23][O:19][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][N:5]3[CH:6]=[CH:7][N:8]=[C:4]3[CH2:3][CH2:2][OH:1])=[CH:18][CH:17]=2)[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12109498(E)-4-chloromethyl-2-[2-(2,4-difluorophenyl)ethenyl]oxazoleHCID 222593234-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenol

Product 1

HCID 227333592-[1-[4-[4-[[2-[(E)-2-(2,4-difluorophenyl)ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]-1-ethanolYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl ]butyl]phenol (260 mg) in DMF (4 ml), 60% oily sodium hydride (44 mg) was added under ice cooling. After stirring at room temperature for 30 minutes, (E)-4-chloromethyl-2-[2-(2,4-difluorophenyl) ethenyl]oxazole (281 mg) was added under ice cooling. After stirring at room temperature for 3 days, water was added under ice cooling. The precipitate was collected by filtration and washed with water. The precipitate was dissolved in a mixture of ethyl acetate-THF and dried over magnesium sulfate, after which it was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to yield the titled compound (275 mg) as pale-yellow crystals.

Workup

  1. stirringAfter stirring at room temperature for 3 days
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. dissolutionThe precipitate was dissolved in a mixture of ethyl acetate-THF
  5. dry with materialdried over magnesium sulfate
  6. concentrationafter which it was concentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-047adfe6963749d7a269a09afef7b5d0
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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