Methyl iodide → ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1508496Notes

Reaction equation

HRID 1508496 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].[CH3:14]I>C1COCC1>[CH3:14][N:7]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 14296950ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-2-pyrrolecarboxylic acid ethyl ester (100 mg, 0.653 mmol) in THF (2.5 mL), was added NaH (31.3 mg, 0.783 mmol). The mixture was stirred for 10 min and then MeI (0.061 mL, 0.979 mmol) was added dropwise. The resulting mixture was stirred overnight. The reaction was quenched with sat. NH4Cl. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate. 1H NMR (500 MHz, CDCl3): δ 6.77 (s, 1H); 6.58 (s, 1H); 4.28 (q, J=7.1 Hz, 2H); 3.88 (s, 3H); 2.08 (s, 3H); 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. customThe reaction was quenched with sat. NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine (1×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1))

Sources & evidence

ORD record
ord-b04b0124c109414c887776ac9ebb7677
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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