Sulfuric Acid → Methyl 2-(Dimethoxymethyl)pyridine-5-carboxylate

HRID 892836Notes

Reaction equation

HRID 892836 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][N:4]=1)=O.OS(O)(=O)=O.[CH:18]([O:23][CH3:24])([O:21][CH3:22])OC>CO>[CH3:24][O:23][CH:18]([O:21][CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 586269Methyl 6-formylpyridine-3-carboxylate

Product 1

HCID 14459972Methyl 2-(Dimethoxymethyl)pyridine-5-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-formylpyridine-5-carboxylate (2.00 g, 12.1 mmol) in methanol (20 ml) and trimethyl orthoformate (5 ml) was added H2SO4 (conc., 1.5 ml). After refluxing overnight, the reaction was cooled and concentrated to a thick slurry and then poured into saturated NaHCO3 (50 ml). The latter was extracted with ether (3×30 ml) and the combined organic layers dried (MgSO4) and concentrated to afford title product (1.91 g, 75%).

Workup

  1. temperatureAfter refluxing overnight
  2. temperaturethe reaction was cooled
  3. concentrationconcentrated to a thick slurry
  4. additionpoured into saturated NaHCO3 (50 ml)
  5. extractionThe latter was extracted with ether (3×30 ml)
  6. dry with materialthe combined organic layers dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-37b45998f08948c8a52c13569fe486ce
Source dataset
uspto-grants-1992_06
Patent number
US05120754

Reaction notes

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