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

HRID 588512Notes

Reaction equation

HRID 588512 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-e89de35399924a51a8c87293ececb3a9
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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