Water → HCID 140401399, compound

HRID 427996Notes

Reaction equation

HRID 427996 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]([OH:29])[C:25]([O:27][CH3:28])=[O:26].O>CC(C)=O>[CH:1](=[N:8]/[O:9][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]([OH:29])[C:25]([O:27][CH3:28])=[O:26])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12143(Z)-Benzaldehyde oximeHCID 70239328HCID 70239328, compound

Product 1

HCID 140401399HCID 140401399, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Then, benzaldehyde oxime (0.28 g, 2.3 mmol) and potassium carbonate (0.43 g, 3.1 mmol) were added to a solution of methyl 2-bromomethyl-α-hydroxyphenylacetate (0.40 g, 1.5 mmol) in acetone (6 ml), and the mixture was stirred at room temperature for 18 hours. Water was added, and the mixture was extracted with ether, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3/1) to give the desired compound methyl (E)-2-benzylideneaminooxymethyl-α-hydroxyphenylacetate (0.08 g, 17%) as an oil.

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-31e77174f75048738bbb1fc8ffd09553
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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