Water → HCID 23143281, compound

HRID 732220Notes

Reaction equation

HRID 732220 reaction equation
[CH3:1][C:2]1[O:6][C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[N:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].Cl[CH2:20][C:21]1[CH:40]=[CH:39][C:24]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.O>CN(C)C=O>[CH3:1][C:2]1[O:6][C:5]([N:7]([CH2:20][C:21]2[CH:40]=[CH:39][C:24]([CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[CH2:8][CH2:9][CH3:10])=[N:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoateHCID 23143269HCID 23143269, compound

Product 1

HCID 23143281HCID 23143281, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methyl-4-phenyl-N-propyl-1,3-oxazole-2-amine (407 mg, 1.88 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% in oil, 82 mg, 2.04 mmol) at room temperature and the mixture was stirred for 30 min. Methyl 3-[4-[[4-(chloromethyl)benzyl]oxy]phenyl]propanoate (500 mg, 1.57 mmol) was added to the reaction mixture and the mixture was stirred at room temperature for 4 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (251 mg, yield 32%) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 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

Sources & evidence

ORD record
ord-5c24c35354fc4966b2f8c53696eff567
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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