Acetic Acid → Ethyl 3-ethyl-5-formyl-4-methyl-1H-pyrrole-2-carboxylate

HRID 495217Notes

Reaction equation

HRID 495217 reaction equation
[CH2:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].C(O)(=[O:17])C>C1COCC1.O>[CH2:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH:9]=[O:17])[NH:5][C:4]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 606892Ethyl 3-ethyl-4,5-dimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 11789030Ethyl 3-ethyl-5-formyl-4-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-ethyl-4,5-dimethyl-1H-pyrrole-2-carboxylate (Salor-Aldrich) (0.0147 g, 0.077 mmol) in acetic acid (5 mL), THF (4 mL) and water (4 mL) was added ceric ammonium nitrate (0.169 g, 0.31 mmol) and the reaction was stirred at ambient temperature. After 1.5 h, the reaction was poured into water (10 mL) and extracted with CH2Cl2 (3×5 mL). The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated. The resultant residue was purified by normal phase chromatography. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CDCl3) δ 9.78 (s, 1H); 4.36 (q, J=7.1 Hz, 2H); 2.76 (q, J=7.6 Hz, 2H); 1.62 (s, 3H); 1.38 (t, J=7.1 Hz, 3H); 1.13 (t, J=7.6 Hz, 3H). HRMS (ES) exact mass calculated for C11H16NO3 (M+H+): 209.1052. Found 209.1050.

Workup

  1. extractionextracted with CH2Cl2 (3×5 mL)
  2. washThe combined organic layers were washed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant residue was purified by normal phase chromatography

Sources & evidence

ORD record
ord-f4aeb51993f74c668e7e158739e3411d
Source dataset
uspto-grants-2009_05
Patent number
US07538231B2

Reaction notes

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