Dichloromethane → ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate

Participants

Reaction Steps

A solution of 54 (3.74 g, 16.91 mmol) and TosMIC (3.30 g, 16.92 mmol) in DMSO/Et2O (1:2, 33 mL) was added via cannula to a vigorously stirred suspension of NaH (842 mg, 35.1 mmol) in Et2O (15 mL) under argon. Stirring was continued for 3 h. Brine and CH2Cl2 were added in small portions. The aqueous layer was extracted with CH2Cl2. The organic extract was washed with brine. The solvent was removed at reduced pressure, and the oily residue was chromatographed [silica, CH2Cl2/ethyl acetate (9:1)] to yield a brown solid (3.23 g, 84%): 1H NMR δ 1.23-1.29 (m, 3H), 4.20-4.27 (m, 2H), 6.88-6.90 (m, 1H), 7.53-7.55 (m, 1H), 7.64-7.67 (m, 2H), 8.18-8.21 (m, 2H), 8.78 (br, 1H).

Provenance & Evidence