Water → ethyl 1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

HRID 372964Notes

Reaction equation

HRID 372964 reaction equation
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]([F:20])([F:19])[C:9]1[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][NH:12][CH:13]=1.CI.O>O1CCCC1>[CH3:1][N:12]1[CH:13]=[C:9]([C:8]([F:7])([F:19])[F:20])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14370786ethyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459511ethyl 1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of potassium t-butoxide (4.5 g, 0.04 mol) in tetrahydrofuran is treated dropwise with a solution of ethyl 4-(trifluoromethyl)pyrrole-3-carboxylate (8.3 g, 0.04 mol) in tetrahydrofuran over a 20 minute period at 20°-25° C., stirred for 30 minutes, treated dropwise with methyl iodide (5.7 g, 0.04 mol), stirred at room temperature for 24 hours and poured into water. The resultant mixture is extracted with ether and the combined extracts are washed with brine, dried (MgSO4) and concentrated in vacuo to afford a brown oil residue. The residue is distilled using a Kugelrohr distillation apparatus to give a gummy solid at 80°-85° C./0.2 mm Hg. The solid is purified using ether and basic alumina to yield the title compound as a clear oil, 6.37 g (72%), identified by NMR and elemental analyses.

Workup

  1. stirringstirred at room temperature for 24 hours
  2. extractionThe resultant mixture is extracted with ether
  3. washthe combined extracts are washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto afford a brown oil residue
  7. distillationThe residue is distilled
  8. distillationa Kugelrohr distillation apparatus
  9. customto give a gummy solid at 80°-85° C./0.2 mm Hg
  10. customThe solid is purified

Sources & evidence

ORD record
ord-777e3cd617cf4d5f8fa3bbbad1c7c8e0
Source dataset
uspto-grants-1992_11
Patent number
US05162308

Reaction notes

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