Potassium Carbonate → HCID 54177657, compound

HRID 1591139Notes

Reaction equation

HRID 1591139 reaction equation
[CH2:1]([O:3][N:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])[CH3:2].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](=[CH:26][O:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][N:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](=[CH:26][O:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 136025195HCID 136025195, compound

Product 1

HCID 54177657HCID 54177657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.9 g (42 mmol) of 2-hydroxybenzaldehyde O-ethyloxime and 10.0 g (35 mmol) of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate are dissolved in 100 ml of dimethylformamide, and 7.3 g (53 mmol) of potassium carbonate are added. The mixture is stirred at room temperature for 48 hours and then concentrated, and the residue is taken up in methylene chloride. The organic phase is washed with water, dried over MgSO4 and concentrated. The resulting oil is purified by chromatography on silica gel (cyclohexane/ethyl acetate). 8.4 g (65% of theory) of the title compound are obtained in the form of colorless crystals (melting point 86°-88° C., compound no. 23).

Workup

  1. concentrationconcentrated
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting oil is purified by chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-7420b90e0d924a0f9b5f3c5d59c7dcdc
Source dataset
uspto-grants-1993_04
Patent number
US05206266

Reaction notes

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