Tolmetin → Allyl 5-(4-methylbenzoyl)-1-methylpyrrole-2-acetate

HRID 618319Notes

Reaction equation

HRID 618319 reaction equation
[Na].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[N:15]([CH3:16])[C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:8]=1.[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[N:15]([CH3:16])[C:14]([CH2:17][C:18]([O:20][CH2:23][CH:22]=[CH2:21])=[O:19])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 5509TolmetinHCID 7841Allyl bromideHCID 5360545Sodium

Product 1

HCID 15870191Allyl 5-(4-methylbenzoyl)-1-methylpyrrole-2-acetateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sodium salt of tolmetin (15.0 g, 47.6 mmol) and allyl bromide (4.3 ml, 49.9 mmol) were dissolved in DMF (50 ml) and the mixture was stirred at room temperature until the esterification was complete (~30 h). The solvent was removed in vacuo and the residue was partitioned between ether and water. The organic layer was separated, washed with water, 1 M sodium hydroxide, and brine, and dried over sodium sulfate. Evaporation gave allyl 5-(4-methylbenzoyl)-1-methylpyrrole-2-acetate (11.97 g, 85%) as a solid. ##STR26##

Workup

  1. custom(~30 h)
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between ether and water
  4. customThe organic layer was separated
  5. washwashed with water, 1 M sodium hydroxide, and brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation

Sources & evidence

ORD record
ord-9857c8b131c9428e92d1df45111ef9aa
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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