Potassium Carbonate → Methyl methoxyimino-[2-(3-methoxyimino-2,3-dihydrobenzofuran-6-yloxymethyl)-phenyl]acetate

HRID 1596146Notes

Reaction equation

HRID 1596146 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]Br)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH3:23][O:24][N:25]=[C:26]1[C:30]2[CH:31]=[CH:32][C:33]([OH:35])=[CH:34][C:29]=2[O:28][CH2:27]1>CN(C)C=O>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:35][C:33]1[CH:32]=[CH:31][C:30]2[C:26](=[N:25][O:24][CH3:23])[CH2:27][O:28][C:29]=2[CH:34]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetateHCID 1359949623-Methoxyimino-6-hydroxy-2,3-dihydrobenzofuran

Product 1

HCID 86757390Methyl methoxyimino-[2-(3-methoxyimino-2,3-dihydrobenzofuran-6-yloxymethyl)-phenyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.4 g of (E) methyl methoxyimino-(2-bromomethylphenyl)acetate was added to 9.0 g of potassium carbonate and 1.8 g of 3-methoxyimino-6-hydroxy-2,3-dihydrobenzofuran in 30 ml of N,N-dimethylformamide, and they were reacted at room temperature for 6 hours. After the completion of the reaction, the reaction liquid was poured in ice/water. After the extraction with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by the silica gel chromatography (hexane:ethyl acetate) to obtain 3.0 g of the title compound (having a m. p. of 108-110° C. and 1H-NMR data shown in the following table).

Workup

  1. customwere reacted at room temperature for 6 hours
  2. customAfter the completion of the reaction
  3. customthe reaction liquid
  4. extractionAfter the extraction with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by the silica gel chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-db623e241ba04f24ae93fa4aecc9f2f2
Source dataset
uspto-grants-2001_09
Patent number
US06291399B1

Reaction notes

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