Lithium Hydroxide → 4-(1-Methylpyrrol-2-ylmethyl)nitrobenzene

HRID 618324Notes

Reaction equation

HRID 618324 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)C(OC)=O.[OH-].[Li+]>CO.C1COCC1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23285895Methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate

Product 1

HCID 232857944-(1-Methylpyrrol-2-ylmethyl)nitrobenzeneYield 83.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate (3.8 g, 14.0 mmol) [prepared as in Example 7, Step (a)] was dissolved in a 1:1 mixture of MeOH-THF (100 ml) and cooled in an ice bath under argon. A solution of 0.4 M lithium hydroxide (69 ml) was added and the reaction mixture was stirred at room temperature. After 2 h, the reaction mixture was poured into 1 M HCl/ice and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The solid residue was redissolved in DMF (40 ml) and heated at reflux. After 20 min the reaction mixture was poured into ice/water and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated to dryness. Purification on a Florisil® column (hexane-ethyl acetate, 9:1) gave 4-(1-methylpyrrol-2-yl-methyl)nitrobenzene (2.53 g, 82%) as a solid. ##STR40##

Workup

  1. temperaturecooled in an ice bath under argon
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe solid residue was redissolved in DMF (40 ml)
  7. temperatureheated
  8. temperatureat reflux
  9. additionAfter 20 min the reaction mixture was poured into ice/water
  10. extractionextracted with ethyl acetate
  11. washThe organic layer was washed with water
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated to dryness
  14. customPurification on a Florisil® column (hexane-ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-fd83c236371c4398a7e01fb3cc42281f
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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