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

Participants

Reaction Steps

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).

Provenance & Evidence