Potassium Carbonate → HCID 18433373, compound

HRID 1372604Notes

Reaction equation

HRID 1372604 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:20])[CH:12]=[C:13]([O:18][CH3:19])[C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:13]([O:18][CH3:19])[C:14]=1[N+:15]([O-:17])=[O:16])[O:20][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 184333963-Benzyloxy-5-methoxy-4-nitrophenol

Product 1

HCID 18433373HCID 18433373, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml), 3-benzyloxy-5-methoxy-4-nitrophenol (1.43 g, 5.20 mmol), potassium carbonate (1.08 g, 7.79 mmol) and methyl bromoacetate (591 μl, 6.24 mmol) were stirred at room temperature for 2 days. The reaction mixture was poured in water (200 ml), followed by extraction with ether (200 ml). The extract was washed with saturated brine (200 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (20:1) eluate fractions, the title compound (1.53 g, 85%) was obtained as a yellow crystalline solid.

Workup

  1. extractionfollowed by extraction with ether (200 ml)
  2. washThe extract was washed with saturated brine (200 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (20:1) eluate fractions

Sources & evidence

ORD record
ord-9fd9b397fcd04aa69f759b8aa073b845
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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