Water → 1-{4-[4-({2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazol-4-yl}methoxy)phenyl]butyl}-1H-1,2,3-triazole

HRID 2084390Notes

Reaction equation

HRID 2084390 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:20][C:21]1[N:22]=[C:23](/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[O:24][CH:25]=1.O>CN(C=O)C>[F:34][C:31]1[CH:32]=[CH:33][C:28](/[CH:27]=[CH:26]/[C:23]2[O:24][CH:25]=[C:21]([CH2:20][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[CH:15][CH:14]=3)[N:22]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 121098664-chloromethyl-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazole

Product 1

HCID 120948331-{4-[4-({2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazol-4-yl}methoxy)phenyl]butyl}-1H-1,2,3-triazoleYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an argon atmosphere, 4-[4-(1H-1,2,3-triazol-1-yl)butyl]phenol (218 mg) and 65% oily sodium hydride (39 mg) were dissolved in DMF (5 ml) added thereto. With stirring under ice cooling, 4-(chloromethyl)-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazole (250 mg) was added, followed by stirring at room temperature for 3 hours. After water was added, the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saturated saline and dried over sodium sulfate, after which it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform-ethanol=24:1), after which it was recrystallized from ethyl acetate to yield the titled compound (368 mg) as colorless crystals.

Workup

  1. additionadded
  2. stirringby stirring at room temperature for 3 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationafter which it was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform-ethanol=24:1)
  8. customafter which it was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-705c5e817002476d82b42f2470dc2211
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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