Potassium Carbonate → Dimethyl 5-(2-methoxy-2-oxoethoxy)-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylate

HRID 2389911Notes

Reaction equation

HRID 2389911 reaction equation
[OH:1][C:2]1[C:3]([C:18]([O:20][CH3:21])=[O:19])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CC(C)=O>[CH3:33][O:32][C:30](=[O:31])[CH2:29][O:1][C:2]1[C:3]([C:18]([O:20][CH3:21])=[O:19])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59179398Dimethyl 5-hydroxy-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylate

Product 1

HCID 59179452Dimethyl 5-(2-methoxy-2-oxoethoxy)-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of dimethyl 5-hydroxy-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylate (5.10 g, 17.2 mmol) and potassium carbonate (12.3 g, 69.0 mmol) in acetone (100 mL) was added methyl bromoacetate (3.26 mL, 34.4 mmol) at room temperature, and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (5.14 g, yield 81%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-0896918d0e8c489297311ce6848476ad
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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