Sodium Methoxide → Dimethyl 3-hydroxy-5-(3-methoxy-3-oxopropyl)furo[2,3-c]pyridine-2,4-dicarboxylate

HRID 2389912Notes

Reaction equation

HRID 2389912 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[C:7]([C:22](OC)=[O:23])=[C:8]([C:18]([O:20][CH3:21])=[O:19])[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[N:10][CH:11]=1.C[O-].[Na+]>CO>[OH:23][C:22]1[C:7]2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[N:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:3]([O:2][CH3:1])=[O:26]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59179452Dimethyl 5-(2-methoxy-2-oxoethoxy)-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylate

Product 1

HCID 59179443Dimethyl 3-hydroxy-5-(3-methoxy-3-oxopropyl)furo[2,3-c]pyridine-2,4-dicarboxylateYield 67.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of dimethyl 5-(2-methoxy-2-oxoethoxy)-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylate (2.20 g, 5.96 mmol) in methanol (60 mL) was added sodium methoxide (0.805 g, 14.9 mmol) at 80° C., and the mixture was stirred for 30 min. The resulting precipitate was collected by filtration, washed with methanol, and dissolved in 1M hydrochloric acid (10 mL). The mixture was extracted with ethyl acetate and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by recrystallization (ethyl acetate/diisopropyl ether) to give the title compound (1.35 g, yield 67%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with methanol
  3. dissolutiondissolved in 1M hydrochloric acid (10 mL)
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by recrystallization (ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-c97cdbf6fd8945be9069f6f7b37da0ed
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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