Potassium Carbonate → HCID 86746755, compound

HRID 1591140Notes

Reaction equation

HRID 1591140 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)[CH3:6])[CH3:2].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+]>CN(C)C=O>[CH2:1]([O:3][N:4]=[C:5]([C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][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])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 54074217HCID 54074217, compound

Product 1

HCID 86746755HCID 86746755, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

7.5 g (0.042 mol) of 3-(1-ethoxyiminoethyl)phenol and 10.0 g (0.035 mol) methyl α-(2-bromomethylphenyl)-β-methoxyacrylate are dissolved in 100 ml of dimethylformamide, and 7.3 g (0.053 mol) of potassium carbonate are added. The mixture is stirred at room temperature (20° C.) for 48 hours, hydrolyzed with water and extracted with diethyl ether. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The resulting oil is purified by chromatography on alumina (cyclohexane). 7.3 g (54%) of the title compound are obtained as a colorless oil (compound no. 447).

Workup

  1. extractionhydrolyzed with water and extracted with diethyl ether
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting oil is purified by chromatography on alumina (cyclohexane)

Sources & evidence

ORD record
ord-84d7bb0ecbab4d3ca0ece254a7ddc17b
Source dataset
uspto-grants-1993_04
Patent number
US05206266

Reaction notes

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