Dimethyl Sulfate → Methyl 5-t-butyl-1-methyl-3-nitropyrrole-2-carboxylate

Participants

Reaction Steps

To a cold (0-10° C.) solution of methyl 5-tert-butyl-3-nitropyrrole-2-carboxylate (0.100 g, 0.44 mmol), benzyltributylammonium bromide (0.16 mg, 0.44 mmol, 1 equiv), and dimethyl sulfate (46 μL, 0.49 mmol, 1.1 equiv) in CH2Cl2 (1 mL) was added a 50% NaOH solution (0.21 g, 2.65 mmol, 6 equiv). After 5 min, the cooling bath was removed and the mixture was stirred at room temp. for 4 h. The reaction mixture was diluted with CH2Cl2, washed with water and a 10% NH4OAc solution (2x), dried (Na2SO4), and concentrated under reduced pressure to give a bright yellow oil. The oil was purified by flash chromatography (70% CH2Cl2/hexane) to give methyl 5-tert-butyl-1-methyl-3-nitropyrrole-2-carboxylate as a pale yellow oil which solidifies upon standing (0.061 g, 62%): 1H NMR (CDCl3) δ1.38 (s, 9H)., 3.80 (s, 3H), 3.92 (s, 3H), 6.47 (s, 1H).

Provenance & Evidence