Potassium Carbonate → HCID 53642905, compound

HRID 1603960Notes

Reaction equation

HRID 1603960 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:13])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[CH:26][O:27][CH3:28])[C:23]([O-:25])=[O:24].[C:29](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:8][N:9]=[C:10]([O:13][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[CH:26][O:27][CH3:28])[C:23]([O:25][CH3:29])=[O:24])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18327285HCID 18327285, compoundHCID 73517220HCID 73517220, compound

Product 1

HCID 53642905HCID 53642905, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-benzyloxypropionamide (1.8 g, 10 mmol), 2-bromomethylphenyl-3-methoxypropenoate (2.85 g, 10 mmol), potassium carbonate (1.66 g, 12 mmol), 4-N,N-dimethyl-aminopyridine (0.1 g) and acetonitrile (20 ml) was heated with reflux for 7 hours. After completion of the reaction, the reaction solution was filtered, the solvent was removed by evaporation, and the residue was purified with silica gel chromatography to obtain methyl 2-[2-{(1-benzyloxyiminopropyl)oxymethyl}phenyl]-3-methoxypropenoate (1.00 g, yield: 26%). The proton NMR Spectra: 1.04 t (3H); 2.21 q (2H); 3.67 s (3H); 3.73 s (3H); 5.01 s (2H); 5.10 s (2H); 7.13-7.45 m (9H); 7.54 s (1H) (Solvent: CDCl3).

Workup

  1. temperaturewas heated
  2. temperaturewith reflux for 7 hours
  3. customAfter completion of the reaction
  4. filtrationthe reaction solution was filtered
  5. customthe solvent was removed by evaporation
  6. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-6075d0e4dc7140eabf6fe70fc09aaf8f
Source dataset
uspto-grants-1999_11
Patent number
US05990161

Reaction notes

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