Methyl iodide → 2-Methyl-1-phenyl-pyrrole

HRID 2263664Notes

Reaction equation

HRID 2263664 reaction equation
[CH2:1]([Li])CCC.[C:6]1([N:12]2[CH:16]=[CH:15][CH:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(CCN(C)C)C.IC>CCCCCC.C1COCC1.O>[C:6]1([N:12]2[CH:16]=[CH:15][CH:14]=[C:13]2[CH3:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 124801-PhenylpyrroleHCID 178418339Butyllithium

Product 1

HCID 46530262-Methyl-1-phenyl-pyrroleYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Butyllithium (0.700 mol, 280 mL of 2.5 M solution in hexane) was added slowly at room temperature to a mixture of 1-phenylpyrrole (0.695 mol, 100 g) and TMEDA (0.700 mol, 106 mL) in hexane (80 mL) and stirred for 3 h. The slurry was diluted with 300 mL of THF and iodomethane (0.771 mol, 48 mL) was added slowly maintaining the temperature between 35-40 C. After stirring at room temperature for 16 h, 250 mL of water were added and the organic layer was separated. The aqueous layer was extracted with ether (2×100 mL) and the combined organic fractions were dried over MgSO4. After filtration, evaporation of solvents and TMEDA yielded 107 g of light brown oil (98% yield, +95% purity by GC). 1H-NMR δ (CDCL3): 7.29-7.44 (m, 5H), 6.80 (m, 1H), 6.23 (m, 1H), 6.08 (m, 1H), 2.24 (s, 3H).

Workup

  1. additionwas added slowly
  2. temperaturemaintaining the temperature between 35-40 C
  3. stirringAfter stirring at room temperature for 16 h
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with ether (2×100 mL)
  6. dry with materialthe combined organic fractions were dried over MgSO4
  7. filtrationAfter filtration, evaporation of solvents and TMEDA

Sources & evidence

ORD record
ord-bf4c2f612ce64ddda6dacea1cf9693d1
Source dataset
uspto-grants-2010_12
Patent number
US07851644B2

Reaction notes

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