Dimethylformamide → Methyl 1-methylpyrrole-2-carboxylate

Participants

Reaction Steps

To 1-methylpyrrole-2-carboxylic acid (28.66 g., 0.229 mol) in 75 ml. DMF at 0° was added N-ethyl diisopropylamine (39.4 ml., 0.229 mol) followed by CH3I (14.27 ml., 0.229 mol). The reaction mixture was stirred 16 hours at room temperature, diluted with equal volumes each of ethyl acetate and water, the pH adjusted from 3.4 to 8.5, and the layers evaporated. The aqueous layer was washed 1×100 ml. fresh ethyl combined, washed 2×100 ml. H2O and 1×100 ml. brine, dried over Na2SO4 and stripped to yield title product as an oil, 24.83 g.; 1H-nmr (CDCl3) delta 3.75 (s, 3H), 3.87 (s, 3H), 5.97 (m, 1H), 6.62 (m, 1H), 6.78 (m, 1H).

Provenance & Evidence