Methyl iodide → 2,4-Dicarbethoxy-1,3-dimethylpyrrole

HRID 2289218Notes

Reaction equation

HRID 2289218 reaction equation
[C:1]([C:6]1[NH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=1[CH3:11])([O:3][CH2:4][CH3:5])=[O:2].[C:17]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[C:1]([C:6]1[N:7]([CH3:17])[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=1[CH3:11])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 226731Diethyl 3-methyl-1h-pyrrole-2,4-dicarboxylate

Product 1

HCID 234463842,4-Dicarbethoxy-1,3-dimethylpyrroleYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2, 4-dicarbethoxy-3 methylpyrrole (25) (2.44 g, 10.9 mmol), K2CO3 (9.9 g), and iodomethane (55 ml) in 750 ml acetone was refluxed at 50° C. for 15 hours. The solution was concentrated in vacuo, partitioned between 450 ml of dichloromethane and 600 ml of water. The aqueous layer was extracted with CH2Cl2 (2×500 ml), dried (sodium sulfate), and concentrated in vacuo to yield a brown oil that solidified upon standing at room temperature for several minutes and was used without further purification. (2.37 g, 91% yield). TLC (benzene) Rf 0.3; 1H NMR (CD2Cl2) δ 7.31 (s, 1H), 4.23 (m, 4H), 3.84 (s, 3H). 2.54 (2, 3H), 1.33 (m, 6H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompartitioned between 450 ml of dichloromethane and 600 ml of water
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×500 ml)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto yield a brown oil that
  7. waitupon standing at room temperature for several minutes
  8. customwas used without further purification

Sources & evidence

ORD record
ord-b0304360c5b04ab2bd77ce4185186eb2
Source dataset
uspto-grants-2000_07
Patent number
US06090947

Reaction notes

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