Water → HCID 86754177, compound

HRID 581106Notes

Reaction equation

HRID 581106 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[CH:27][O:28][CH3:29])[C:24]([O-:26])=[O:25].O.[CH3:31]N(C)C=O>>[CH2:1]([O:8][N:9]=[C:10]([O:12][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[CH:27][O:28][CH3:29])[C:24]([O:26][CH3:31])=[O:25])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 5129184N-phenylmethoxyacetamideHCID 73517220HCID 73517220, compound

Product 1

HCID 86754177HCID 86754177, compoundYield 9.2%

Procedure

A solution of N-benzyloxyacetamide (1.65 g, 10 mmol) in 10 ml of dimethylformamide was cooled down in an ice bath, 60% sodium hydride (0.4 g, 10 mmol) was added thereto, and stirred for 10 minutes. After adding dropwise 20 ml of dimethylformamide solution of 2-bromomethylphenyl-3-methoxypropenoate (2.85 g, 10 mmol), the solution was allowed to react for 15 hours at room temperature. After completion of the reaction, the reaction solution was poured into 200 ml of water, and extracted with ethylacetate. The organic layer was rinsed with water and dried. After removing the solvent by evaporation, the residue was purified with silica gel chromatography to obtain 0.34 g of methyl 2-[2-(1-benzyloxyiminoethyl) oxymethylphenyl]-3-methoxypropenoate (yield: 9.2%). The proton NMR spectrum is 1.79 s (3H); 3.67 s (3H); 3.77 s (3H); 5.01 s (2H); 5.04 s (2H); 7.10-7.50 m (9H); 7.57 s (1H) (solvent: CDCl3).

Workup

  1. customto react for 15 hours at room temperature
  2. customAfter completion of the reaction
  3. extractionextracted with ethylacetate
  4. washThe organic layer was rinsed with water
  5. customdried
  6. customAfter removing the solvent
  7. customby evaporation
  8. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-a0bc1266b0964ce3ba26cf712bac6c0b
Source dataset
uspto-grants-1999_07
Patent number
US05919825

Reaction notes

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