Allyl bromide → HCID 57855834, compound

HRID 475575Notes

Reaction equation

HRID 475575 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:27])[CH2:11][CH2:12][C:13]1[N:14]=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([OH:26])[CH:19]=2)[O:16][CH:17]=1)[CH3:2].N12CCCN=C1CC[CH2:31][CH2:30][CH2:29]2.C(Br)C=C>C(O)C>[CH2:31]([O:26][C:20]1[CH:19]=[C:18]([C:15]2[O:16][CH:17]=[C:13]([CH2:12][CH2:11][C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[O:3][CH2:1][CH3:2])=[O:27])[N:14]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25])[CH:30]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68982042HCID 68982042, compound

Product 1

HCID 57855834HCID 57855834, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.3 g quantity of 1-(2-ethoxyphenyl)-3-[2-(3-hydroxy-4-methoxyphenyl)oxazol-4-yl]propan-1-one obtained in Example 101 was suspended in 10 ml of ethanol, 0.37 g of 1,8-diazabicyclo[5,4,0]undec-7-ene and 0.14 ml of allyl bromide were added thereto, and stirring was conducted for 3 hours while heating and refluxing. After distilling off ethanol under reduced pressure, water was added, ethyl acetate extraction was performed, followed by drying over anhydrous magnesium sulfate and distilling the solvent off. The residue was subjected to silica gel column purification (n-hexane:ethyl acetate=3:1), thereby yielding 0.2 g of white powdery 3-[2-(3-allyloxy-4-methoxyphenyl)oxazol-4-yl]-1-(2-ethoxyphenyl)propan-1-one.

Workup

  1. temperaturewhile heating
  2. temperaturerefluxing
  3. distillationAfter distilling off ethanol under reduced pressure, water
  4. additionwas added
  5. extractionethyl acetate extraction
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationdistilling the solvent off
  8. customThe residue was subjected to silica gel column purification (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ff956f72975749a693a6ca645c11371f
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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