Water → methyl 5-formyl-1-methyl-1H-pyrrole-3-carboxylate

HRID 1037973Notes

Reaction equation

HRID 1037973 reaction equation
[CH:1]([C:3]1[NH:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1)=[O:2].[CH3:12]C(C)([O-])C.[K+].CI.O>CN(C=O)C>[CH:1]([C:3]1[N:7]([CH3:12])[CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1)=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 579027Methyl 5-formylpyrrole-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14173855methyl 5-formyl-1-methyl-1H-pyrrole-3-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-formyl-1H-pyrrole-3-carboxylate (60.0 g, 0.360 mol) in DMF (60 mL) was added potassium tert-butoxide (72.0 g, 0.576 mol). After stirring at rt for 30 min, the mixture was cooled to 0° C. and methyl iodide (132 mL, 1.45 mol) was added. The solution was then stirred at rt overnight. Water was added to quench the reaction and the solution was extracted with DCM (3×200 mL). The combined organic phases were washed with brine (50 mL), dried (Na2SO4), and concentrated to give methyl 5-formyl-1-methyl-1H-pyrrole-3-carboxylate (45.0 g, 80%). 1H NMR (CDCl3, 400 MHz) δ 12.62 (s, 1H), 9.48 (s, 1H), 7.66 (s, 1H), 7.30 (s, 1H), 3.67 (s, 3H).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringThe solution was then stirred at rt overnight
  3. customto quench
  4. customthe reaction
  5. extractionthe solution was extracted with DCM (3×200 mL)
  6. washThe combined organic phases were washed with brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b9090638e8ff4ceab73b9c219f3808ee
Source dataset
uspto-grants-2013_10
Patent number
US08546588B2

Reaction notes

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