Ethyl Acetate → HCID 19746239, compound

HRID 2253738Notes

Reaction equation

HRID 2253738 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:8](=[O:24])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1.[C:33](OCC)(=[O:35])C.C([O-])(=O)C.[Na+]>CN(C)C=O>[CH3:6][N:7]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:8](=[O:24])[CH2:9][C:10]1[CH:11]=[C:12]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:13]=[CH:14][C:15]=1[CH:33]=[O:35]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 10594635HCID 10594635, compound

Product 1

HCID 19746239HCID 19746239, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (1.61 ml, 0.0173 mol) is added dropwise to 1.34 ml of N,N-dimethylformamide (DMF) while the reaction mixture is maintained between 10° to 20° C. with an external cooling bath. A solution of N-methyl-N-phenethyl-2-(3-benzyloxyphenyl)acetamide (3.73 g, 0.0144 mol) in DMF is added dropwise, the resulting mixture is heated at 100° C. for 6 hours. After cooling to room temperature, the reaction mixture is poured into an ice/H2O mixture, ethyl acetate is added, followed by 7.3 g of sodium acetate. The resulting mixture is stirred for 1 hour. The layers are separated. The organic layer is washed with 10 ml of 1N aqueous HCl and brine; dried (MgSO4) and concentrated concentrated in vacuo. The residue obtained is purified by a flash column packed with silica gel and eluted with 5% ethyl acetate in CH2Cl2 to give N-methyl-N-phenethyl-2-(5-benzyloxy-2-formylphenyl)acetamide. NMR confirms this structure.

Workup

  1. temperatureis maintained between 10° to 20° C. with an external cooling bath
  2. temperatureAfter cooling to room temperature
  3. additionis added
  4. customThe layers are separated
  5. washThe organic layer is washed with 10 ml of 1N aqueous HCl and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. concentrationconcentrated in vacuo
  9. customThe residue obtained
  10. customis purified by a flash column
  11. washeluted with 5% ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-885c3f2eaad74bd19e4fa72c60941a2c
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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