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

HRID 1265494Notes

Reaction equation

HRID 1265494 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) δ7.31 (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-5d494d1d54a7425791a971a1e90c2a1e
Source dataset
uspto-grants-2003_04
Patent number
US06545162B1

Reaction notes

Loading…