Water → HCID 57855853, compound

HRID 475576Notes

Reaction equation

HRID 475576 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].Br[CH:29]([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[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]([O:26][CH:29]([CH3:31])[CH3:30])[CH:19]=2)[O:16][CH:17]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 68982042HCID 68982042, compound

Product 1

HCID 57855853HCID 57855853, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 5.0 g quantity of 1-(2-ethoxyphenyl)-3-[2-(3-hydroxy-4-methoxyphenyl)oxazol-4-yl]propan-1-one obtained in Example 101 was dissolved in 50 ml of dimethylformamide, 3.35 g of 2-bromopropane and 5.63 g of potassium carbonate were added thereto, and stirring was conducted overnight at room temperature. Water was added to the obtained mixture, 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=4:1), and the obtained crude crystals were recrystallized using ethanol, thereby yielding 2.99 g of white powdery 1-(2-ethoxyphenyl)-3-[2-(3-isopropoxy-4-methoxyphenyl)oxazol-4-yl]propan-1-one.

Workup

  1. dry with materialby drying over anhydrous magnesium sulfate
  2. distillationdistilling the solvent off
  3. customThe residue was subjected to silica gel column purification (n-hexane:ethyl acetate=4:1)
  4. customthe obtained crude crystals
  5. customwere recrystallized

Sources & evidence

ORD record
ord-d82b52ea859f4786b760bb70ae4a2b0f
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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