Hydrochloric Acid → 4-[4-[2-(E)-[2-(2,4-difluorophenyl)ethenyl]-1,3-oxazol-4-yl]methoxyphenyl]-1-butanol

HRID 2084388Notes

Reaction equation

HRID 2084388 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:16][C:17]1[N:18]=[C:19](/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])[O:20][CH:21]=1.Cl>CN(C=O)C.O>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1/[CH:23]=[CH:22]/[C:19]1[O:20][CH:21]=[C:17]([CH2:16][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=2)[N:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 12109498(E)-4-chloromethyl-2-[2-(2,4-difluorophenyl)ethenyl]oxazoleHCID 133925134-(4-Hydroxybutyl)phenol

Product 1

HCID 227333504-[4-[2-(E)-[2-(2,4-difluorophenyl)ethenyl]-1,3-oxazol-4-yl]methoxyphenyl]-1-butanolYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-hydroxyphenyl)-1-butanol (1.99 g) in DMF (20 ml), 60% oily sodium hydride (528 mg) was added under ice cooling, followed by stirring at room temperature for 30 minutes. Under ice cooling, (E)-4-chloromethyl-2-[2-(2,4-difluorophenyl)ethenyl]oxazole (3.37 g) was added, followed by stirring overnight at room temperature. After water and 1 N hydrochloric acid was added, the reaction mixture was extracted with ethyl acetate. After the extract was dried over magnesium sulfate, it was concentrated under reduced pressure; the residue was recrystallized from ethyl acetate-diethyl ether-hexane to yield the titled compound (3.71 g) as colorless crystals.

Workup

  1. stirringby stirring overnight at room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialAfter the extract was dried over magnesium sulfate, it
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate-diethyl ether-hexane

Sources & evidence

ORD record
ord-39ec23e024444ce9a638466212ed91e7
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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