Water → 2-[(E)-2-(4-fluorophenyl)ethenyl]-4-[[4-[4-[2-[2-(methylsulfanyl)ethyl]-1H-imidazol-1-yl]butyl]phenoxy]methyl]-1,3-oxazole

HRID 1610966Notes

Reaction equation

HRID 1610966 reaction equation
[H-].[Na+].[CH3:3][S:4][CH2:5][CH2:6][C:7]1[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH:9]=[CH:10][N:11]=1.Cl[CH2:24][C:25]1[N:26]=[C:27](/[CH:30]=[CH:31]/[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[O:28][CH:29]=1.O>CN(C=O)C>[F:38][C:35]1[CH:36]=[CH:37][C:32](/[CH:31]=[CH:30]/[C:27]2[O:28][CH:29]=[C:25]([CH2:24][O:22][C:19]3[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:8]4[CH:9]=[CH:10][N:11]=[C:7]4[CH2:6][CH2:5][S:4][CH3:3])=[CH:17][CH:18]=3)[N:26]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 121098664-chloromethyl-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazoleHCID 222593154-[4-[2-[2-(methylsulfanyl)ethyl]-1H-imidazol-1-yl]butyl]phenol

Product 1

HCID 222593362-[(E)-2-(4-fluorophenyl)ethenyl]-4-[[4-[4-[2-[2-(methylsulfanyl)ethyl]-1H-imidazol-1-yl]butyl]phenoxy]methyl]-1,3-oxazoleYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

65% Sodium hydride (63.1 mg) was added to a solution of 4-[[4-[4-[2-[2-(methylsulfanyl)ethyl]-1H-imidazol-1-yl]butyl]phenol (300 mg) in DMF (5 ml) at 0° C., and the mixture was stirred at room temperature for 30 min. 4-Chloromethyl-2-[(E) -2-(4-fluorophenyl)ethenyl]-1,3-oxazole (269 mg) was added to the mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:3 to ethyl acetate) to give the titled compound (374 mg) as a colorless amorphous form.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:3 to ethyl acetate)

Sources & evidence

ORD record
ord-e27084920456420ea2b4e4b0e51ae4e9
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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