Water → HCID 57855799, compound

HRID 475628Notes

Reaction equation

HRID 475628 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])=[O:18])[N:14]=2)=[CH:6][C:5]=1[OH:28].[CH2:30]1[CH2:40]CN2C(=NCCC2)[CH2:32][CH2:31]1.BrCCC=C.O>C(O)C.C(OCC)(=O)C>[CH2:32]([O:28][C:5]1[CH:6]=[C:7]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])=[O:18])[N:14]=2)[CH:8]=[CH:9][C:4]=1[O:3][CH:2]([F:1])[F:29])[CH2:31][CH:30]=[CH2:40]

Participants

7

Reactant 4

HCID 962WaterHCID 21241Homoallyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68984934HCID 68984934, compound

Product 1

HCID 57855799HCID 57855799, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0.12 g quantity of the compound obtained in Example 229 and 0.14 ml of DBU were dissolved in 3 ml of ethanol, 0.12 g of 4-bromo-1-butene was then added to the obtained solution, and heating and refluxing were conducted overnight. After cooling, water was added to the obtained reaction mixture, and ethyl acetate extract was performed. The organic layer was washed twice with water, concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1). The obtained crystals were recrystallized from ethanol, thereby yielding 80 mg of white powdery 3-[2-(3-but-3-enyloxy-4-difluoromethoxyphenyl)oxazol-4-yl]-1-(2-ethoxyphenyl)propan-1-one.

Workup

  1. temperatureheating
  2. temperaturerefluxing
  3. temperatureAfter cooling
  4. extractionextract
  5. washThe organic layer was washed twice with water
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)
  8. customThe obtained crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-2e990727239043c4af8c2dab0b5ab221
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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