Hydrochloric Acid → HCID 22934531, compound

HRID 1354417Notes

Reaction equation

HRID 1354417 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.C([Li])(C)(C)C.I[C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1.Cl>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=2)=[CH:4][CH:5]=[C:6]1[C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 142891Ethyl 4-iodobenzoateHCID 22934551HCID 22934551, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 22934531HCID 22934531, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (5 ml) of 1-methyl-2-(4-trifluoromethylphenyl)pyrrole (1.13 g) in tetrahydrofuran was added dropwise t-butyl lithium (1.7 M solution in pentane, 3.00 ml) under an argon atmosphere at −78° C. This mixed solution was heated to room temperature, and a solution (10 ml) of zinc chloride (0.756 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and ethyl 4-iodobenzoate (0.381 ml) and tetrakis (triphenylphosphine)palladium (0.144 g) were added. This mixture was stirred overnight under an argon atmosphere and poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1, volume ratio) and recrystallized from hexane-ethyl acetate to give ethyl 4-[1-methyl-5-(4-trifluoromethylphenyl)-2-pyrrolyl]benzoate (0.573 g, yield 31%) as colorless needle crystals. melting point: 150–151° C.

Workup

  1. stirringThis mixture was stirred overnight under an argon atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1, volume ratio)
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-1e17f899ded54ae4a012efc0d5a145ce
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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