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

HRID 618344Notes

Reaction equation

HRID 618344 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>[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 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate (9.2 g, 33.54 mmol) [prepared as in Example 21, Step (a)], was dissolved in methanol (100 ml) and an aqueous solution of lithium hydroxide (3.52 g in 50 ml of water) was added. After 1.5 h the reaction mixture was concentrated to dryness in vacuo and the resulting residue was dissolved in water (100 ml). The solution was acidified to pH 1 with 6 M HCl and then extracted with ethyl acetate. The organic extracts were washed with water, and brine, and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by flash chromatography (hexane-ethyl acetate, 9:1) to give 4-(1-methylpyrrol-2-ylmethyl)nitrobenzene (4.8 g, 66%) as a yellow oil. ##STR63##

Workup

  1. concentrationAfter 1.5 h the reaction mixture was concentrated to dryness in vacuo
  2. dissolutionthe resulting residue was dissolved in water (100 ml)
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography (hexane-ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-52d9efb4fc2c47be840b4f1a4a0233c4
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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