Potassium Carbonate → HCID 86752938, compound

HRID 1957532Notes

Reaction equation

HRID 1957532 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](=[N:12][OH:13])[CH3:11])=[N:2]1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[CH:27][O:28][CH3:29])[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](=[N:12][O:13][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22](=[CH:27][O:28][CH3:29])[C:23]([O:25][CH3:26])=[O:24])[CH3:11])=[N:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 136351318HCID 136351318, compound

Product 1

HCID 86752938HCID 86752938, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.8 g of 1-(1,2-benzisoxazol-3-yl)ethanone oxime, 1.3 g of methyl 2-(bromomethyl)-α-(methoxymethylene)phenylacetate and 1 g of potassium carbonate in 15 ml of acetonitrile is refluxed for 4 h. The reaction mixture is cooled and filtered and the filtrate is concentrated under vacuum. The residue is dissolved in ethyl acetate and the solution is washed twice with water and once with a saturated solution of sodium chloride and dried over sodium sulfate. After removal of the solvent under vacuum, the residue is purified by chromatography on silica gel with ethyl acetate/hexane (1:3), giving the title compound having a melting point of 97°-98° C.

Workup

  1. temperatureis refluxed for 4 h
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated under vacuum
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washthe solution is washed twice with water and once with a saturated solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customAfter removal of the solvent under vacuum
  9. customthe residue is purified by chromatography on silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-0cc99ea2e0a44b829a9e6f5b3df9c44c
Source dataset
uspto-grants-1998_07
Patent number
US05786374

Reaction notes

Loading…