Water → HCID 57855753, compound

HRID 475591Notes

Reaction equation

HRID 475591 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:28])[CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]([CH3:27])[CH3:26])[CH:17]=2)[O:14][CH:15]=1.[CH2:29](Br)[CH:30]=[CH2:31].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:31]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:28])[CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]([CH3:26])[CH3:27])[CH:17]=2)[O:14][CH:15]=1)[CH:30]=[CH2:29]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromide2×HCID 11430Potassium CarbonateHCID 57855862HCID 57855862, compound

Product 1

HCID 57855753HCID 57855753, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 67 mg quantity of 1-(2-hydroxyphenyl)-3-[2-(3-isopropoxy-4-methoxyphenyl)oxazol-4-yl]propan-1-one obtained in Example 223 was dissolved in 5 ml of dimethylformamide. A 31 μl quantity of allyl bromide and 73 mg of potassium carbonate were added thereto, and the mixture was stirred at room temperature overnight. A 50 μl quantity of allyl bromide was further added thereto, and the mixture was stirred at 50° C. for 8 hours, and at room temperature overnight. The reaction mixture was added to water, and extraction was then performed with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate 3:1), and crystallized from n-hexane to give 33 mg of colorless powdery 1-(2-allyloxyphenyl)-3-[2-(3-isopropoxy-4-methoxyphenyl)oxazol-4-yl]propan-1-one.

Workup

  1. stirringthe mixture was stirred at 50° C. for 8 hours
  2. customat room temperature
  3. customovernight
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate 3:1)
  8. customcrystallized from n-hexane

Sources & evidence

ORD record
ord-7cd07eb7316a4431b0e3b35ab667406b
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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